[ CAS No. 20781-20-8 ] {[proInfo.proName]}

Name: 20781-20-8|(2,4-Dimethoxyphenyl)methanamine|98%
Brand: Ambeed
SKU: A273191
Rating: 90 (29 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 20781-20-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 20781-20-8 ]

Product Details of [ 20781-20-8 ]

CAS No. :	20781-20-8	MDL No. :	MFCD00052393
Formula :	C₉H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QOWBXWFYRXSBAS-UHFFFAOYSA-N
M.W :	167.21	Pubchem ID :	597250
Synonyms :

Calculated chemistry of [ 20781-20-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.1
TPSA :	44.48 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.0
Log Po/w (XLOGP3) :	1.25
Log Po/w (WLOGP) :	1.01
Log Po/w (MLOGP) :	0.92
Log Po/w (SILICOS-IT) :	1.44
Consensus Log Po/w :	1.32

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.44 mg/ml ; 0.0146 mol/l
Class :	Very soluble
Log S (Ali) :	-1.78
Solubility :	2.76 mg/ml ; 0.0165 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.69
Solubility :	0.341 mg/ml ; 0.00204 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.28

Safety of [ 20781-20-8 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	2735
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 20781-20-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 20781-20-8 ]
Downstream synthetic route of [ 20781-20-8 ]

[ 20781-20-8 ] Synthesis Path-Upstream 1~8

1
[ 31874-34-7 ]
[ 20781-20-8 ]

Reference： [1] Synthetic Communications, 1995, vol. 25, # 6, p. 863 - 869
[2] Tetrahedron, 2005, vol. 61, # 34, p. 8130 - 8137
[3] Journal of Organic Chemistry, 1971, vol. 36, p. 3966 - 3970
[4] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 24 - 33

2
[ 613-45-6 ]
[ 20781-20-8 ]

Reference： [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6197 - 6208
[2] Tetrahedron, 2005, vol. 61, # 34, p. 8130 - 8137
[3] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 24 - 33

3
[ 20781-21-9 ]
[ 20781-20-8 ]

Reference： [1] Patent: WO2004/113275, 2004, A2, . Location in patent: Page 174

4
[ 4107-65-7 ]
[ 20781-20-8 ]
[ 20781-23-1 ]

Reference： [1] Synthetic Communications, 2002, vol. 32, # 8, p. 1265 - 1269

5
[ 4107-65-7 ]
[ 20781-20-8 ]

Reference： [1] Chemische Berichte, 1968, vol. 101, # 10, p. 3623 - 3641

6
[ 20781-20-8 ]
[ 613-45-6 ]
[ 20781-23-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃;	2,4-dimethoxybenzaidehyde (Sigma Aldrich; 1.1 g, 661 mmoi) wasdissolved in 20 rnL THF at ambient temperature. To the solution was added 2,4- dimethoxybenzyiamine (Sigma Aldrich; 1.5 rnL, 9.98 mrnol) followed by sodium triacetoxyborohydride (Sigma Aldrich; 1 7 g; 8.4 inmol) and the mixture(increasingly cloudy) was stirred at ambient temperature overnight. The mixturewas then diluted with sat. NaHCO3 and extracted with EtOAc, dried over MgSO4and concentrated. The residue was purified by chromatography on 40 g ISCOcolumn eluting with a gradient of 0 to 100percent EtOAc to deliver bis(2,4-dimethoxybenzyi)amine (2.08 g, 6.55 mrnol, 99percent yield, 96percent purity)
8 g	Stage #1: at 20℃; for 2 h; Stage #2: With sodium tris(acetoxy)borohydride In ethanol at 20℃; for 1 h;	A) bis(2,4-dimethoxybenzyl)amine A solution of 2,4-dimethoxybenzylamine (8.98 mL) and 2,4-dimethoxybenzaldehyde (9.94 g) in ethanol (200 mL) was stirred at room temperature for 2 hr. To the reaction mixture was added sodium triacetoxyborohydride (20.3 g), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8 g). ¹H NMR (300 MHz, DMSO-d₆) δ2.01 (1H, brs) 3.55 (4H, s) 3.74 (6H, s) 3.75 (6H, s) 6.46 (2H, dd, J=8.1, 2.3 Hz) 6.51 (2H, d, J=2.3 Hz) 7.18 (2H, d, J=8.1 Hz).

Reference： [1] Patent: WO2017/147410, 2017, A1, . Location in patent: Page/Page column 1832
[2] Tetrahedron Letters, 2010, vol. 51, # 28, p. 3645 - 3648
[3] Chemische Berichte, 1968, vol. 101, # 10, p. 3623 - 3641
[4] Patent: US2013/131050, 2013, A1, . Location in patent: Paragraph 0570; 0571
[5] Patent: WO2018/97945, 2018, A1, . Location in patent: Paragraph 0395

7
[ 4107-65-7 ]
[ 20781-20-8 ]
[ 20781-23-1 ]

Reference： [1] Synthetic Communications, 2002, vol. 32, # 8, p. 1265 - 1269

8
[ 20781-20-8 ]
[ 20781-23-1 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 37, p. 7610 - 7617

[ 20781-20-8 ] Synthesis Path-Downstream 1~88

1
[ 383-70-0 ]
[ 20781-20-8 ]
[ 20781-35-5 ]

Reference： [1]Chemische Berichte,1968,vol. 101,p. 3623 - 3641

2
[ 4107-65-7 ]
[ 20781-20-8 ]

Reference： [1]Chemische Berichte,1968,vol. 101,p. 3623 - 3641

3
[ 4107-65-7 ]
[ 20781-20-8 ]
[ 20781-23-1 ]

Reference： [1]Synthetic Communications,2002,vol. 32,p. 1265 - 1269

4
[ 20781-20-8 ]
[ 10111-08-7 ]
(2,4-Dimethoxy-benzyl)-[1-(1H-imidazol-2-yl)-meth-(Z)-ylidene]-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2255 - 2259

5
[ 1003-32-3 ]
[ 20781-20-8 ]
(2,4-Dimethoxy-benzyl)-[1-thiazol-5-yl-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3209 - 3215

6
[ 20781-20-8 ]
[ 132684-59-4 ]
[ 345347-68-4 ]
5-(4-formyl-3,5-dimethoxyphenoxy)valeric aldehyde linker on a polyethylene glycol resin [ No CAS ]
2-butyl-N¹-[1-(2,4-dimethoxy-benzylcarbamoyl)-3-phenyl-propyl]-N⁴-hydroxy-succinamide [ No CAS ]

Reference： [1]Antimicrobial Agents and Chemotherapy,2004,vol. 48,p. 250 - 261

7
[ 20781-20-8 ]
[ 1912-24-9 ]
N²-(2,4-dimethoxybenzyl)-N⁴-ethyl-N⁶-isopropyl-1,3,5-triazine-2,4,6-triamine [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2005 - 2008

8
[ 20781-20-8 ]
[ 71989-26-9 ]
[ 79-08-3 ]
[ 146982-24-3 ]
H-Tyr(tBu)-Ile-2Cl-Trt-PS resin [ No CAS ]
H-Val-Lys(Boc)-Asp(OAll)-(Dmb)Gly-Tyr(tBu)-Ile-OH [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4121 - 4124

9
[ 20781-20-8 ]
[ 175422-04-5 ]
(2,6-dibromo-pyridin-4-yl)-(2,4-dimethoxy-benzyl)-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 113 - 117

10
[ 20781-20-8 ]
[ 55864-87-4 ]
2,4-dimethoxybenzylamine salt of N-(2,4-dimethoxybenzyl)-4-nitro-1H-pyrazole-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 120℃; for 1.5h;	[00847] Step 2: Preparation of N-(2, 4-Dimethoxybenzyl)-4-nitro-1H- pyrazole-3-carboxamide; [00849] The carboxylate from Step 1 (3.32 g, 17.93 mmol) was stirred in excess 2, 4-dimethoxybenzylamine at 120 C for 1.5 h. The resulting product was triturated with hot EtOH and filtered to give 8.45 g of product as the 2,4- dimethoxybenzylamine salt (1: 1). The salt was dissolve in MeOH (300 mL, 60 C for 0.5 h), acidified using conc. HCI and diluted to a total volume of 1 L with water. The resulting precipitate was filtered, rinsed with water and air-dried to give an off-white solid.'H NMR (300 MHz, DMSO-d6) : No. 3.74 (s, 3 H), 3.79 (s, 3 H), 4.33 (d, 2 H), 6.50 (m, 2 H), 7.19 (d, 1 H), 8. 8 (br s, 1 H), 8.87 (br s, 1 H), 14.05 (br s, 1 H); MS (ESI+) for C, 3H, 4N4O5 m/z 307.0 (M+H) +.

Reference： [1]Patent: WO2005/37797,2005,A1 .Location in patent: Page/Page column 272-273

11
[ 20781-20-8 ]
[ 66684-61-5 ]
[ 862270-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 70℃; for 20.0h;	A mixture of <strong>[66684-61-5]1,5-difluoro-3-methoxy-2-nitrobenzene</strong> from step (b) above (4.00 g, 21.2 mmol), 2,4-dimethoxybenzylamine (3.18 mL, 21.2 mmol, Aldrich) and triethylamine (2.96 ml, 21.2 mmol) in THF (210 mL) was heated at 70 C. for 20 h. The reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. The residue was dissolved in CH2Cl2 and passed through a pad of silica gel, eluting with CH2Cl2. The CH2Cl2 solution was evaporated under reduced pressure and the residue was dried in vacuo to give the title compound as a yellow solid. MS (ESI, pos. ion.) m/z: 359 (M+23).

Reference： [1]Patent: US2005/176726,2005,A1 .Location in patent: Page/Page column 30

12
[ 5926-51-2 ]
[ 20781-20-8 ]
[ 541-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid;	Scheme C-6 illustrates the synthesis of the maleimide pyrazole scaffold C-63 wherein R4 is hydrogen. The synthesis starts with the condensation reaction of <strong>[5926-51-2]bromomaleic anhydride</strong> B77 with 2,4-dimethoxybenzylamine in acetic acid and acetic anhydride, giving rise to intermediate B78.
	In acetic acid;	Scheme C-6 illustrates the synthesis of the maleimide pyrazole scaffold C-63 wherein R4 is hydrogen. The synthesis starts with the condensation reaction of <strong>[5926-51-2]bromomaleic anhydride</strong> B77 with 2,4-dimethoxybenzylamine in acetic acid and acetic anhydride, giving rise to intermediate B78.

Reference： [1]Patent: US6423713,2002,B1
[2]Patent: US6514977,2003,B1

13
[ 20781-20-8 ]
[ 51997-51-4 ]
1-(9H-carbazol-4-yloxy)-3-[(2,4-dimethoxybenzyl)-amino]propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.2%	In ipa; ethyl acetate; for 4.5h;Heating / reflux;	To a stirred solution of Epoxy carbazole (5gm, 0.0209 mole) in IPA (20 ml), 2,4-dimethoxybenzylamine (9.42 ml, 0.06276 moles) was added, and the reaction mixture was heated to reflux for 3 hours. Subsequently the reaction mixture was cooled and IPA was stripped off. To the semisolid residue obtained, ethyl acetate (50 ml) was added and it was refluxed for 1.5 hours, until everything dissolved. A light yellow colored clear solution was finally obtained, which was stirred at room temperature for 5 hours when it completely crystallized out as a white solid (8 g, 94.2%), m.p: 152-154 0C, 1H NMR (400 MHz, CDCl3): delta 2.89(m IH), 2.99(d IH), 3.74(s 3H), 3.78(s 3H), 3.8 l(d 2H), 4.27(m, 3H)5 6.42(m 2H), 6.65(d IH), 7.08(d IH), 7.14(m 2H), 7.29(m IH), 7.35(d IH), 7.43(d IH), 8.22(d IH), 9.42(s IH); m/zM+1406.

Reference： [1]Patent: WO2007/42912,2007,A2 .Location in patent: Page/Page column 20

14
[ 20781-20-8 ]
[ 51997-51-4 ]
(2R)-1-(9H-carbazol-4-yloxy)-3-[(2,4-dimethoxybenzyl)-amino]propan-2-ol [ No CAS ]
(2S)-1-(9H-carbazol-4-yloxy)-3-[(2,4-dimethoxybenzyl)-amino]propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; for 3h;Heating / reflux;	Step 2: Preparation of 1-(9H-carbazol-4-yloxy)-3-[(2,4-dimethoxybenzyl)amino]propan-2-ol To a stirred solution of Epoxy carbazole (5 gm, 0.0209 mole) in IPA (20 ml), 2,4-dimethoxybenzylamine (9.42 ml, 0.06276 moles) was added, and the reaction mixture was heated to reflux for 3 hours. Subsequently the reaction mixture was cooled and IPA was stripped off. To the semisolid residue obtained, ethyl acetate (50 ml) was added and it was refluxed for 1.5 hours, until everything dissolved. A light yellow colored clear solution was finally obtained, which was stirred at room temperature for 5 hours when it completely crystallized out as a white solid (8 g, 94.2%), m.p: 152-154 C., 1H NMR (400 MHz, CDCl3): delta 2.89(m 1H), 2.99(d 1H), 3.74(s 3H), 3.78(s 3H), 3.81(d 2H), 4.27(m, 3H), 6.42(m 2H), 6.65(d 1H), 7.08(d 1H), 7.14(m 2H), 7.29(m 1H), 7.35(d 1H), 7.43(d 1H), 8.22(d 1H), 9.42(s 1H); m/zM+1 406.

Reference： [1]Patent: US2007/111998,2007,A1 .Location in patent: Page/Page column 10

15
[ 120-57-0 ]
[ 1026147-10-3 ]
[ 20781-20-8 ]
[ 112811-65-1 ]
[ 1026147-16-9 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 3966 - 3974

16
[ 23100-12-1 ]
[ 1026147-10-3 ]
[ 20781-20-8 ]
[ 112811-65-1 ]
[ 1026147-15-8 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 3966 - 3974

17
[ 98-03-3 ]
[ 3622-04-6 ]
[ 14542-93-9 ]
[ 20781-20-8 ]
C₃₁H₃₇N₃O₄S₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 5324 - 5327

18
[ 20781-20-8 ]
[ 1885-81-0 ]
[ 10165-86-3 ]
[ 501-52-0 ]
[ 947756-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	In trifluoroethanol; at 20℃; for 4h;	Step A: Methyl 6-{2-[(4-chlorophenyl)amino]-1-[(2,4-dimethoxybenzyl)(3-phenylpropanoyl)-amino]-2-oxoethyl}nicotinate Dihydrocinnamic acid (46 mg, 0.30 mmol), 4-chlorophenylisocyanide (42 mg, 0.30 mmol) and 2,4-dimethoxybenzylamine (61 mg, 0.36 mmol) were added to a solution of methyl 6-formylnicotinate (see Langlois, Y. et al, Tetrahedron. 1975, 31, 419-22) (50 mg, 0.30 mmol) in 400 muL of TFE. The solution was allowed to stir for 4 h at room temperature and then purified by flash chromatography (12-100percent ethyl acetate in hexanes to give the desired product. MS cal'd 602 (MH+), exp 602 (MH+).

Reference： [1]Patent: US2009/69250,2009,A1 .Location in patent: Page/Page column 48

19
[ 90272-84-7 ]
[ 20781-20-8 ]
[ 1192814-30-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	In dimethyl sulfoxide; at 150℃; for 0.5h;Microwave irradiation;	Step A: N-(2,4-Dimethoxybenzyl)-7-methylquinoxalin-2-amine <strong>[90272-84-7]2-Chloro-7-methylquinoxaline</strong> (0.51 g, 2.86 mmol), ), prepared according to J. Chem. Soc. 1948 1310-1313, and (2,4-dimethoxyphenyl)methanamine (1.29 mL, 8.57 mmol) were microwaved in DMSO (2.5 mL) for 30 min at 150 C. This was diluted into 150 mL EtOAc and extracted three times with 100 mL brine. The crude product was purified by flash chromatography on a 90 g silica gel cartridge with 20 to 80% EtOAc in hexane, 50 min, at 40 mL/min to afford N-(2,4-dimethoxybenzyl)- 7-methylquinoxalin-2-amine (860 mg, 2.78 mmol, 97 % yield).1H NMR (400 MHz, CDCl3) delta ppm 8.08 (1 H, s), 7.70 (1 H, d, J=8.31 Hz), 7.49 (1 H, s), 7.30 (1 H, d, J=8.06 Hz), 7.17 (1 H, dd, J=8.31, 2.01 Hz), 6.47 (1 H, d, J=2.52 Hz), 6.42 (1 H, dd, J=8.31, 2.52 Hz), 5.23 (1 H, t, J=5.16 Hz), 4.63 (2 H, d, J=5.79 Hz), 3.83 (3 H, s), 3.78 (3 H, s), 2.48 (3 H, s).LCMS: RT = 1.93 min, MH+ = 310.20.
97%	In dimethyl sulfoxide; at 150℃; for 0.5h;Microwave irradiation;	<strong>[90272-84-7]2-Chloro-7-methylquinoxaline</strong> (0.51 g, 2.86mmol), prepared according to J. Chem. Soc. 1948 13101313, and (2,4-dimethoxyphenyl)methanamine (1.29 ml.,8.57 mmol) were microwaved in DMSO (2.5 mL) for 30 min at 150 C. This was diluted into 150 mL EtOAc and extracted three times with 100 mL brine. The crude product was purifiedby flash chromatography on a 90 g silica gel cartridge with 20 to 80% EtOAc in hexane, 50 min, at 40 mUmin toafford N-(2,4-dimethoxybenzyl)-7-methylquinoxalin-2-amine(860 mg, 2.78 mmol, 97% yield).

Reference： [1]Patent: WO2011/53292,2011,A1 .Location in patent: Page/Page column 247
[2]Patent: JP5714745,2015,B2 .Location in patent: Paragraph 0440; 0441

20
[ 20781-20-8 ]
[ 5334-40-7 ]
[ 850727-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 20h;	4-Nitro-1H-pyrazole-3-carboxylic acid 2,4-dimethoxybenzylamide is obtained in the following manner:23 g of 2,4-dimethoxybenzylamine and then 20.04 g of 98percent <strong>[5334-40-7]4-nitro-3-pyrazolecarboxylic acid</strong> are added to a solution of 28.76 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 20.27 g of 1-hydroxybenzotriazole in 100 ml of dimethylformamide. The reaction medium is stirred for at room temperature for 20 hours. The clear yellow solution obtained is then poured into 1000 ml of distilled water. A white suspension is obtained, which is left at room temperature for 1 hour. The suspension is filtered and the filter cake is washed with three times 250 ml of distilled water. The solid obtained is drained by suction and dried in air and then in a Heraeus oven under vacuum (temp. 40° C. P: 0.2 mbar). 40.65 g of a white solid are obtained, which product is triturated in 750 ml of refluxing isopropanol for 20 minutes. The suspension obtained is cooled in a bath of water+ice for 2 hours, and then filtered off. The filter cake is washed with twice 100 ml of isopropanol and then twice 100 ml of isopropyl ether. The solid obtained is dried in air and then in a Heraeus oven (temp. 40° C. P: 0.2 mbar). 32.16 g of <strong>[5334-40-7]4-nitro-1H-pyrazole-3-carboxylic acid</strong> 2,4-dimethoxybenzylamide are obtained in the form of a white solid melting at 204° C. ([M+H]+): 307). RT: 3.12 min Example 35: 4-(ethyl{3-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]benzyl}amino)-1H-pyrazole-3-carboxamide
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20℃; for 16h;	4-Nitro-1H-pyrazole-3-(2,4-dimethoxybenzylamide) A solution of 14.65 g (76.4 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide dihydrate and 10.32 g (76.4 mmol) of 1-hydroxybenzotriazole in 50 ml of dimethylformamide is stirred at ambient temperature. 11.7 g (70.03 mmol) of 2,4-dimethoxybenzylamine are added, then 10.2 g of 4-nitro-3-pyrazole carboxylic acid are added in small portions. After 16 hours of stirring at ambient temperature, the reaction medium is poured into 500 ml of water. The suspension is filtered, then washed with 2.x.250 ml of water. The solid obtained is dried in an oven under vacuum at 40° C. in order to give 18.58 g of 4-nitro-1H-pyrazole-3-(2,4-dimethoxybenzylamide) in the form of a white solid.1H NMR (400 MHz, DMSO-d) delta ppm 3.75 (s, 3H) 3.80 (s, 3H) 4.35 (d, J=5.9 Hz, 2H) 6.50 (dd, J=8.3, 2.4 Hz, 1H) 6.56 (d, J=2.4 Hz, 1H) 7.21 (d, J=8.3 Hz, 1H) 8.71 (broad s, 1 H) 8.88 (broad t, J=5.9 Hz, 1H) 14.13 (broad unresolved m, 1H)MS (ES+/-) Retention time Tr (min)=3.23; [M+H]+ m/z=307; [M-H]- m/z=305Melting point (Kofler): 192° C.

Reference： [1]Patent: US2009/291984,2009,A1 .Location in patent: Page/Page column 22-23
[2]Patent: US2012/270918,2012,A1 .Location in patent: Page/Page column 6

21
[ 20781-20-8 ]
[ 133446-99-8 ]
[ 1214900-77-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	To a solution of the above product in 40 ml DMF at rt was added 2,4- dimethoxybenzyl amine (2.7 ml, 17.98 mmol, 1.2 eq.), potassium carbonate (4.1 g, 30.12 mmol, 2 eq.) and the mixture stirred overnight at rt. It was diluted with ethyl acetate, washed 2x with water, 1 N HCI, brine, dried over MgSO4, filtered, concentrated and purified by chromatography using 5% ethyl acetate in dichloromethane to provide 2.43 g of P29.

Reference： [1]Patent: WO2011/17296,2011,A1 .Location in patent: Page/Page column 66

22
[ 6925-00-4 ]
[ 20781-20-8 ]
quinoxaline-6-carboxylic acid 2,4-dimethoxy-benzylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Protocol B:The acid derivative (1.0 eq.) is dissolved in a mixture of DMF and DIEA (3.0 to 5.0 eq.). A solution of TBTU (1.3 eq.) and HOBt (0.3 eq.) in DMF is added and the mixture is stirred at room temperature for 5 to 30 minutes. The amine (1.0 eq.) is added and the reaction mixture is stirred at room temperature for a period of 20 min to 24 hours. DMF is removed under reduced pressure. The residue is diluted with EtOAc or DCM and washed with 0.5N HCI, 0.5N NaOH and water/brine or with 1 N NaHCO3 and water/brine or with 1 N Na2CO3 and water/brine. The organic layer is dried over MgSO4 and the solvent is removed under reduced pressure. The residue is purified by flash chromatography, semi-prep HPLC or by recrystallization.

Reference： [1]Patent: WO2007/138112,2007,A2 .Location in patent: Page/Page column 36; 43

23
[ 149057-19-2 ]
[ 20781-20-8 ]
[ 1311150-53-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3142 - 3147

24
[ 1187-59-3 ]
[ 20781-20-8 ]
[ 1307612-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 140℃; for 0.5h;Microwave irradiation;	General procedure: A solution of <strong>[1187-59-3]N-methylacrylamide</strong> (2) (1.88 g, 22.0 mmol) and cyclopentylamine (1.98 mL, 20.0 mmol) in MeOH (14 mL) was heated under microwave irradiation to 140 C for 30 min (Biotage Initiator). The volatiles were removed under reduced pressure, the residue diluted with MeOH (20 mL) and purified by strong cation exchange filtration (50 g SCX-2 cartridge) washing with MeOH (100 mL) and eluting with 7 M methanolic NH3 (100 mL). The eluted product was concentrated under reduced pressure to afford the title compound 3 as a brown oil (3.09 g, 18.2 mmol, 91%). This was used directly with no further purification.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 5049 - 5055

25
[ 171096-33-6 ]
[ 20781-20-8 ]
[ 1226804-63-2 ]

Reference： [1]Synthesis,2012,vol. 44,p. 2396 - 2400

26
[ 20781-20-8 ]
[ 93683-65-9 ]
[ 1403741-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; at 20℃; for 1.5h;	Step 1 : To an ice-cooled solution of 6-chloro-2-cyano-3-nitropyridine (52.0 g, 283 mmol) and triethylamine (43.0 ml_, 425 mmol) in EtOH (950 ml_) was added dropwise 2,4- dimethoxybenzylamine (53.2 ml_, 312 mmol). The reaction was stirred at ambient temperature for 1.5 hours. The precipitate was filtered and washed with petrol to afford 75 g of 6-(2,4-dimethoxy-benzylamino)-3-nitro-pyridine-2-carbonitrile as a yellow solid. NMR 1H NMR (400 MHz, Me-d3-OD): 8.19 (1 H, d), 7.24 (1 H, d), 6.77 (1 H, d), 6.57 (1 H, d), 6.49 (1 H, dd), 4.56 (2H, s), 3.86 (3H, s), 3.80 (3H, s). MS: [M+H]+ = 315.

Reference： [1]Patent: WO2012/143725,2012,A1 .Location in patent: Page/Page column 120

27
[ 372198-69-1 ]
[ 20781-20-8 ]
[ 1432912-80-5 ]

Yield	Reaction Conditions	Operation in experiment
20%	In toluene; at 120℃; for 48h;Sealed tube;	B. To a solution of ethyl 6-bromoimidazo[1 ,2-a]pyridine-3-carboxylate (1.0 g, 3.7 mmol) in toluene (5 mL) was added 2,4-dimethoxybenzylamine (0.93 g, 5.6 mmol). The reaction mixture was heated at 120 C for 2 days in a sealed tube, allowed to cool to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-100% gradient of ethyl acetate in hexanes to afford 6-bromo-/V-(2,4-dimethoxybenzyl)imidazo[1 ,2-a]pyridine-3-carboxamide as a yellow oil in 20% yield (0.29 g): H NMR (300 MHz, CDCI3) £9.70-9.67 (m, 1 H), 7.91 (s, 1 H), 7.53 (dd, J = 9.5, 0.7 Hz, 1 H), 7.38 (dd, J = 9.5, 1.9 Hz, 1 H), 7.27-7.21 (m, 2H), 6.48-6.38 (m, 2H), 4.54 (d, J = 5.8 Hz, 2H), 3.85 (s, 3H), 3.78 (s, 3H); MS (ES+) m/z 389.8 (M + 1), 391.8 (M + 1). C. Following the procedure as described in EXAMPLE 4 and making non- critical variations to replace 5-bromo-7-(4-methoxybenzyl)imidazo[1 ,5-a]pyrazin-8(7H)- one with 6-bromo-A/-(2,4-dimethoxybenzyl)imidazo[1 ,2-a]pyridine-3-carboxamide, 6-(5- chloro-2-hydroxyphenyl)-//-(2,4-dimethoxybenzyl)imidazo[1 ,2-a]pyridine-3- carboxamide was obtained as a beige solid in 70% yield (0.226 g): 1H NMR (300 MHz, CDCI3) £9.77 (br s, 1 H), 9.54 (s, 1 H), 7.90 (s, 1 H), 7.50 (s, 2H), 7.25-7.20 (m, 1 H), 7.12-7.04 (m, 2H), 6.98-6.86 (m, 2H), 6.37-6.33 (m, 1 H), 6.29-6.23 (m, 1 H), 4.37 (d, J = 4.5 Hz, 2H), 3.74 (s, 3H), 3.68 (s, 3H); MS (ES+) m/z 437.8 (M + 1), 439.8 (M + 1).

Reference： [1]Patent: WO2013/64984,2013,A1 .Location in patent: Page/Page column 81

28
[ 20781-20-8 ]
[ 153034-94-7 ]
[ 1357916-23-4 ]

Yield	Reaction Conditions	Operation in experiment
61%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 110℃; for 16h;Inert atmosphere;	A mixture of <strong>[153034-94-7]2-fluoro-4-iodo-5-methylpyridine</strong> (1.0 g, 4.2 mmol), 2,4-dimethoxybenzylamine (2.0 g, 12.6 mmol), and DIEA (1.6 g, 12.6 mmol) in 1,4-dioxane (5 mL) was heated at 110 C. for 16 h under Ar gas. The reaction was concentrated to dryness. The crude product was purified by flash chromatography (Biotage, 20 g column, PE/EA=5:1) to give N-[(2,4-dimethoxyphenyl)methyl]-4-iodo-5-methyl-pyridin-2-amine (1.0 g, 61% yield) as a yellow solid. LCMS (ESI) [M+H]+=250.0.
50%	at 110℃;	Step 1: N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine A solution of <strong>[153034-94-7]2-fluoro-4-iodo-5-methylpyridine</strong> (85 g, 340 mmol) in 1-(2,4-dimethoxyphenyl)methanamine (270 mL, 1.68 mol) was allowed to stir at 110 C. overnight. The reaction mixture was allowed to cool to rt and diluted with EtOAc. A precipitate formed and was filtered and then washed with EtOAc. The solid was purified further by column chromatography to give N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine (138 g, 50%).
50%	at 110℃;	[00183] A solution of <strong>[153034-94-7]2-fluoro-4-iodo-5-methylpyridine</strong> (85 g, 340 mmol) in 1-(2,4- dimethoxyphenyl)methanamine (270 mL, 1.68 mol) was allowed to stir at 110C overnight. The reaction mixture was allowed to cool to ii and diluted with EtOAc. A precipitate formed and was filtered and then washed with EtOAc. The solid was purified further by column chromatography to give N-(2,4- dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine (138 g, 50%).

50%

at 110℃;

Step 1: N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine A solution of [153034-94-7]2-fluoro-4-iodo-5-methylpyridine (85 g, 340 mmol) in 1-(2,4-dimethoxyphenyl)methanamine (270 mL, 1.68 mol) was allowed to stir at 110 C. overnight. The reaction mixture was allowed to cool to rt and diluted with EtOAc. A precipitate formed and was filtered and then washed with EtOAc. The solid was purified further by column chromatography to give N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine (138 g, 50%).

Reference： [1]Patent: US2018/282282,2018,A1 .Location in patent: Paragraph 0989; 0990
[2]Patent: US2013/165464,2013,A1 .Location in patent: Paragraph 0838
[3]Patent: WO2015/108861,2015,A1 .Location in patent: Paragraph 00183
[4]Patent: US2015/225422,2015,A1 .Location in patent: Paragraph 0241-0242

29
[ 20781-20-8 ]
[ 153034-94-7 ]
[ 1357916-25-6 ]

Reference： [1]Patent: US2013/165464,2013,A1
[2]Patent: US2015/225422,2015,A1

30
[ 31169-27-4 ]
[ 20781-20-8 ]
[ 1527518-20-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 12h;	To a solution of the 7-bromo-4-chlorothieno[3,2-d]pyriniidine (1.0 g, 4.0 mmol) obtained in step 3) of Preparation Example 1 in DMF (10 mL) were added dimethoxybenzylamine (0.63 mL, 4.21 mmol) and diisoproylethylamine (1.05 mL, 6.01 mmol), followed by stirring at room temperature for 12 hrs. Ice water was added to the resulting solution to form precipitates, which were filtered and dried at 50°C to obtain the desired compound (1.36 g, 89percent). 'H-NMR(300MHz, DMSO-d6) delta 8.48(s, 1H), 8.43(dd, 1H), 8.30(s, 1H), 7.05(d, 1H), 6.56(d, 1H), 6.42(d, 1H), 4.60(d, 2H), 3.80(s, 3H), 3.72(s, 3H).

Reference： [1]Patent: WO2014/3483,2014,A1 .Location in patent: Page/Page column 22

31
[ 20781-20-8 ]
[ 4025-71-2 ]
[ 1397769-82-2 ]

Yield	Reaction Conditions	Operation in experiment
5 g	In dichloromethane; for 2h;Cooling;	To a solution of <strong>[4025-71-2]2-phenylethanesulfonyl chloride</strong> (3 g) in dichloromethane (50 ml) was slowly added dropwise, at 0 C., 2,4-dimethoxybenzylamine (5 g) dissolved in dichloromethane (5 ml). The cooling was removed and the mixture was stirred for another two hours. The suspension formed was admixed with water (100 ml) and the organic phase was removed. The organic phase was then washed with 2N hydrochloric acid (100 ml) and saturated sodium hydrogencarbonate solution (100 ml), dried (Na2SO4), filtered and concentrated. This gave the product (5 g), which was used without further workup.

Reference： [1]Patent: US2014/66437,2014,A1 .Location in patent: Paragraph 0347; 0348

32
[ 20781-20-8 ]
[ 1204-06-4 ]
[ 1610703-55-3 ]

Yield	Reaction Conditions	Operation in experiment
48%		General procedure: To a solution of the acid derivative (1mmol) in CH2Cl2 were added triethylamine (2mmol) and ethyl chloroformate (1mmol), followed by stirring at 0C for 30min. After addition of the appropriate amine derivative (1.2mmol), the mixture was stirred for an additional 1h at 0C. Then, the reaction mixture was warmed to room temperature and stirred overnight. After the solvent was evaporated under reduced pressure, acetone was added, filtered, and evaporated. The residue was dissolved in CH2Cl2, and the organic phase was washed with a 1% NaHCO3 solution and brine, dried over Na2SO4, and evaporated under vacuum. The final residue was purified by flash column chromatography (Combiflash Rf) using CH2Cl2-MeOH (0-5%) as eluents. 4.3.9 (E)-N-(2,4-Dimethoxybenzyl)-3-(1H-indol-3-yl)acrylamide 3i Yield 48%, mp 164-166 C; IR (FTIR/FTNIR-ATR): 1644 cm-1 (C=O), 3241 cm-1 (N-H). 1H NMR (DMSO-d6) delta: 11.54 (1H, s), 8.07 (1H, t, J = 6 Hz), 7.92 (1H, d, J = 8 Hz), 7.74 (1H, s), 7.61 (1H, d, J = 15.6 Hz), 7.45 (1H, d, J = 7.6 Hz), 7.18 (3H, m), 6.71 (1H, d, J = 16 Hz), 6.57 (1H, s), 6.50 (1H, d, J = 8 Hz), 4.28 (2H, d, J = 5.6 Hz), 3.81 (3H, s), 3.74 (3H, s). 13C NMR (DMSO-d6) delta: 166.9, 160.4, 158.4, 138.0, 133.6, 131.0, 129.8, 125.5, 122.8, 120.9, 120.7, 119.8, 116.9, 112.9, 112.8, 104.9, 98.8, 56.0, 55.8, 37.7; HRMS C20H21N2O3 [M+H]+ Calcd 337.1552, Found m/z 337.1539.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3096 - 3104

33
[ 3622-04-6 ]
[ 20781-20-8 ]
N-(2, 4-dimethoxybenzyl)benzo[d]thiazole-2-carboxamide [ No CAS ]

Reference： [1]MedChemComm,2014,vol. 5,p. 1489 - 1495

34
[ 32137-76-1 ]
[ 20781-20-8 ]
N-(2, 4-dimethoxybenzyl)benzo[d]thiazole-2-carboxamide [ No CAS ]

Reference： [1]MedChemComm,2014,vol. 5,p. 1489 - 1495

35
[ 20781-20-8 ]
[ 76537-18-3 ]
6-chloro-N2-(2,4-dimethoxybenzyl)pyrazine-2,3-diamine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 1531 - 1535

36
[ 5975-12-2 ]
[ 20781-20-8 ]
(4-chloro-3-nitropyridin-2-yl)-(2,4-dimethoxybenzyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium carbonate; In methanol; at 20℃; for 18h;	4-Chloro-3-nitro-pyridin-2-yl)-(2,4-dimethoxy-benzyl [1J002] To the <strong>[5975-12-2]2,4-dichloro-3-nitropyridine</strong> (8.2 g, 42 mmol) in 200 mL of methanol was added the sodium carbonate (9.01 g, 85.0 mmol), follwed by the 2,4-dimethoxybenzyl amine (7.81 g, 46.7 mmol) and strirred at room temp for 18 h. The reaction mixture was concentrated and the crude extracted with EtOAc. The ethylacetate layer was washed with water, brine and dried over anhydrous sodium sulfate, filtered and concentrated. The crude was chromatographed on 330 g ISCO silica gel column using a gradient of Hexane:EtOAc (0-30percent) to give 9.9 g of the compound [J002] (72percent yield).

Reference： [1]Patent: US2015/274720,2015,A1 .Location in patent: Paragraph 0295

37
[ 20781-20-8 ]
2-(((tert-butyldimethylsilyl)oxy)methyl)-3-tosyl-7,8,9,10-tetrahydrocyclohepta[e]indol-6(3H)-one [ No CAS ]
[ 1186-73-8 ]
methyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-10-(2,4-dimethoxybenzyl)-7-hydroxy-9-oxo-1-tosyl-1,4,5,6,9,10-hexahydropyrido[2’,3’:3,4]cyclohepta[1,2-e]indole-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		To a solution of 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-tosyl-7,8,9,10- tetrahydrocyclohepta[e]indol-6(3H)-one (650 mg, 1.3 mmol) in CH2C12 (6 mL) was added 2- ,4-dimethoxybenzylamine (0.22 mL, 1.43 mmol) and triethylamine (0.54 mL, 3.9 mmol). The mixture was cooled to 0 C. To the mixture was added a TiCl4 solution (1 M CH2C12, 0.85 mL, 0.85 mmol) dropwise via syringe over 5 min. The mixture was allowed to warm to room temperature and was stirred overnight. The excess reagent was quenched with aqueous saturated NaHC03 (3 mL). The organic phase was separated with vigorous shaking using a PTFE phase separator, dried over Na2S04, filtered, and concentrated. The residue was combined with <strong>[1186-73-8]trimethyl methanetricarboxylate</strong> (342 mg, 1.8 mmol) in Ph20 (2.6 mL). The mixture was placed in a pre-heated aluminum block at 230 C and stirred for 15 minutes. The reaction vessel was removed from the heating block and allowed to cool to room temperature. The crude reaction mixture was loaded directly onto a silica gel column, eluting with 0-60% EtOAc in hexanes to yield a yellow powder (0.52 g, 52%). LC-MS: 773.4 [M+H]+, RT 1.97 min. 1H NMR (500 MHz, acetone- 6) delta ppm 0.18 (s, 6H), 0.98 (s, 9H), 1.34 (m, 1H), 1.92 (m, 1H), 2.01 (m, 1H), 2.26 (m, 1H), 2.39 (s, 3H), 2.90 (m, 2H), 3.38 (s, 3H), 3.68 (s, 3H), 3.90 (s, 3H), 4.96 (d, J=15.6 Hz, 2H), 5.17 (m, 2H), 6.16 (d, J=8.3 Hz, 1H), 6.30 (d, J=2.3 Hz, 1H), 6.61 (d, J=8.3 Hz, 1H), 6.91 (s, 1H), 7.25 (d, J=8.6 Hz, 1H), 7.43 (d, J=7.8 Hz, 2H), 7.94-8.00 (m, 3H), 13.79 (br. s, 1H).

Reference： [1]Patent: WO2016/25933,2016,A2 .Location in patent: Page/Page column 172

38
[ 20781-20-8 ]
3-tosyl-7,8,9,10-tetrahydrocyclohepta[e]indol-6(3H)-one [ No CAS ]
[ 1186-73-8 ]
methyl 10-(2,4-dimethoxybenzyl)-7-hydroxy-9-oxo-1-tosyl-1,4,5,6,9,10-hexahydropyrido[2’,3‘:3,4]cyclohepta[1,2-e]indole-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		To a solution of 3-tosyl-7,8,9,10-tetrahydrocyclohepta[e]indol-6(3H)-one (670 mg, 1.9 mmol) in CH2C12 (10 mL) was added 2-,4-dimethoxybenzylamine (0.32 mL, 2.1 mmol) and triethylamine (0.79 mL, 5.7 mmol). The mixture was cooled to 0 C. To the mixture was added a TiCl4 solution (1 M CH2C12, 1.24 mL, 1.24 mmol) dropwise via syringe over 5 min. The mixture was allowed to warm to room temperature and was stirred overnight. The excess reagent was quenched with aqueous saturated NaHC03 (5 mL). The organic phase was separated with vigorous shaking using a PTFE phase separator, dried over Na2S04, filtered, and concentrated. The residue was combined with <strong>[1186-73-8]trimethyl methanetricarboxylate</strong> (650 mg, 3.4 mmol) in Ph20 (3.8 mL). The mixture was placed in a pre-heated aluminum block at 220 C and stirred for 15 min. The reaction vessel was removed from the heating block and allowed to cool to room temperature. The crude reaction mixture was loaded directly onto a silica gel column, eluting with 0-100% EtOAc in hexanes to yield a yellow powder (0.58 g, 49%). LC-MS: 629.1 [M+H]+, RT 1.47 min. 1H NMR (500 MHz, acetone- 6) delta ppm 1.33 (m, 1H), 1.87-2.03 (m, 2H), 2.25 (m, 1H), 2.39 (s, 3H), 2.92 (m, 2H), 3.32 (s, 3H), 3.67 (s, 3H), 3.90 (s, 3H), 4.95 (d, J=15.6 Hz, 1H), 5.28 (d, J=15.2 Hz, 1H), 6.15 (m, 1H), 6.27 (m, 1H), 6.62 (d, J=8.2 Hz, 1H), 6.96 (m, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.46 (m, 2H), 7.81 (d, J=8.6 Hz, 1H), 7.91 (d, J=3.8 Hz, 1H), 7.98 (m, 2H), 13.77 (br. s, 1H).

Reference： [1]Patent: WO2016/25933,2016,A2 .Location in patent: Page/Page column 174; 175

39
[ 129790-37-0 ]
[ 20781-20-8 ]
[ 1186-73-8 ]
methyl 9-bromo-1-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydrobenzo[2,3]thiepino[4,5-b]pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		Step 1: Methyl 9-bromo-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-l,2,5,6-tetrahydrobenzo[2,3]thiepino[4,5-b]pyridine-3-carboxylate To a stirring solution of 8-bromo-3,4-dihydrobenzo[b]thiepin-5(2H)-one (Intermediate 9, Step 2, 36.2 g, 141 mmol), (2,4-dimethoxyphenyl)methanamine (25.9 g, 23.3 mL, 155 mmol), triethylamine (42.7 g, 58.7 mL, 423 mmol) in CH2C12(300 mL) at 0 C was added T1CI4(1M CH2C12, 71 mL, 71 mmol) dropwise. After the addition, the mixture was brought to room temperature and stirred overnight. The reaction was quenched with satd. NaHC03solution (3 mL) and the mixture was diluted with CH2C12(120 mL). The CH2C12layer was separated using a phase separator cartridge and the aqueous layer was extracted with CH2C12(2 x 30 mL). The combined organic phases were evaporated to dryness followed by the addition of <strong>[1186-73-8]trimethyl methanetricarboxylate</strong> (53.6 g, 282 mmol) and diphenyl ether (280 mL). The mixture was stirred at 230 C for 15 min., then cooled and chromato graphed (ethyl acetate in hexanes, 0-100 % gradient) to obtain the title compoundas a light brown solid (47.6 g, 64%). LC-MS: 532.0, 534.0 [M+H]+, RT 1.59 min.

Reference： [1]Patent: WO2016/25932,2016,A1 .Location in patent: Page/Page column 125

40
[ 20781-20-8 ]
9-tosyl-3,4-dihydro-2H-thiepino[3,2-f]indol-5(9H)-one [ No CAS ]
[ 1186-73-8 ]
methyl 1-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-9-tosyl-2,5,6,9-tetrahydro-1H-pyrido[2',3':4,5]thiepino[3,2-f]indole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		Step 1: Methyl l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-9-tosyl-2,5,6,9-tetrahydro- 1H-pyrido[2',3':4,5]thiepino[3,2-f]indole-3-carboxylate o a stirring solution of Intermediate 9 (1.02 g, 2.75 mmol), (2,4-dimethoxyphenyl)methanamine (0.51 g, 0.45 mL, 3.03 mmol), triethylamine (0.83 g, 1.14 mL, 8.25 mmol) in CH2C12(6.0 mL) at 0 C was added a solution of TiCl4(1M in CH2C12,1.4 mL, 1.4 mmol) dropwise. After the addition, the mixture was brought to roomtemperature and stirred overnight. The reaction was quenched with satd. NaHC03solution (3 mL) and the mixture was diluted with CH2C12(12 mL). The CH2C12layer was separated and the aqueous layer was extracted with CH2C12(2 x 3 mL). The combined organics were evaporated to dryness followed by the addition of <strong>[1186-73-8]trimethyl methanetricarboxylate</strong> (1.05 g,5.5 mmol) and diphenyl ether (5.0 mL). The mixture was stirred at 230 C for 10 min, then cooled to room temperature and loaded directly onto a silica gel column. The product was chromato graphed (ethyl acetate in CH2C120-50 %) to furnish the title compound as a light brown solid (1.10 g, 62%). LC-MS: 647.2 [M+H]+, RT 1.57 min.

Reference： [1]Patent: WO2016/25932,2016,A1 .Location in patent: Page/Page column 154

41
[ 5400-79-3 ]
[ 20781-20-8 ]
ethyl 3-(2,4-dimethoxybenzylamino)cyclopentanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; at 0 - 20℃; for 14h;	2,4-dimethoxybenzyl amine (556 mg, 4.66 mmol, 1.0 eq.), sodium triacetoxyborohydride (446 mg, 3.32 mmol, 1.4 eq.) and acetic acid (200 mg, 3.32 mmol, 1.0 eq.) were added to a solution of <strong>[5400-79-3]ethyl 3-oxocyclopentanecarboxylate</strong> (520 mg, 3.32 mmol, 1.0 eq.) in tetrahydrofuran (5 mL) at 0 C. The reaction was stirred at room temperature for 14 hours, quenched with saturated NaHCO3 (10 mL). The aqueous phase was extracted with ethyl acetate (10 mL*2). The combined organic phases were dried over anhydrous sodium sulfate, and concentrated to give the crude product, which was purified by silica gel column chromatography (eluent: petroleum ether:ethyl acetate=1:1) to give the title compound (250 mg, yield: 44%).

Reference： [1]Patent: US2016/200730,2016,A1 .Location in patent: Paragraph 0445; 0446

42
[ 20781-20-8 ]
[ 7579-20-6 ]
C₁₅H₁₇N₃O₃ [ No CAS ]

Reference： [1]Patent: WO2016/68580,2016,A2 .Location in patent: Page/Page column 72

43
[ 583878-42-6 ]
[ 20781-20-8 ]
ethyl 4-((2,4-dimethoxybenzyl)amino)-6-methyl-2-(methylthio)pyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In acetonitrile; at 20℃;	Ethyl 4-chloro-6-methyl-2- (methylthio) pyrimidine-5-carboxylate (1.22 g, 5 mmol) , (2, 4-dimethoxyphenyl) methanamine (835 mg, 5 mmol) and Et3N (1.4 mL) were dissolved in CH3CN (50 mL) , the resulting mixture was stirred at rt. overnight, and then concentrated to dryness. The residue was purified by flash column chromatography to afford the title compound as a solid (1.8 g) . Yield: 95. MS (ESI) : calcd. value for C18H23N3O4S is 377.1, m/z measured value is 378.1 (M+1)+.

Reference： [1]Patent: WO2016/119707,2016,A1 .Location in patent: Paragraph 142

44
[ 20781-20-8 ]
2-methyl-5,6,7,8-tetrahydrocyclohepta[d]imidazol-4(1H)-one [ No CAS ]
[ 1186-73-8 ]
methyl 10-(2,4-dimethoxybenzyl)-7-hydroxy-2-methyl-9-oxo-3,4,5,6,9,10-hexahydroimidazo[4’,5’:6,7]cyclohepta[1,2-b]pyridine-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%		TiC14 (1.0 M in CH2C12, 6.44 mL, 6.44 mmol) was added to a solution of 2-methyl-5,6,7,8-tetrahydrocyclohepta[dlinildazol-4(1H)-one (Intermediate 3, step 2, 0.96 g, 5.85 mmol), (2,4- dimethoxyphenyl)methanamine (1.08 g, 6.44 mmol), triethylamine (3.19 g, 4.39 mL, 31.61mmol), and CH2C12 (10.0 mL) at 0 C. The mixture was stirred at 0 C for 0.5 h. The mixture was brought to room temperature and stirred overnight. The reaction was diluted with CH2C12 and quenched with saturated aqueous NaHCO3 The organic phase was separated using a phase separator cartridge. The aqueous layer was extracted with CH2C12. The organic layerswere combined and evaporated to dryness. The residue, <strong>[1186-73-8]trimethyl methanetricarboxylate</strong> (2.22 g, 11.7 mmol), and diphenyl ether (25 mL) were stirred at 200C for 10 mm. The mixture was cooled to room temperature and purified by silica gel column chromatography (0-20% MeOH in CH2C12) followed by reversed phase C18 chromatography, (0-50% acetonitrile in water) to afford the title compound (0.36 g, 14%).LC-MS 438.3 [M-Hf, RT 1.04 mm

Reference： [1]Patent: WO2016/109706,2016,A1 .Location in patent: Page/Page column 246; 247

45
[ 20781-20-8 ]
2-(((tert-butyldimethylsilyl)oxy)methyl)-1-ethyl-5,6,7,8-tetrahydrocyclohepta[d]imidazol-4(1H)-one [ No CAS ]
[ 1186-73-8 ]
methyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-10-(2,4-dimethoxybenzyl)-3-ethyl-7-hydroxy-9-oxo-3,4,5,6,9,10-hexahydroimidazo[4',5':6,7]cyclohepta[1,2-b]pyridine-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		To a solution of the product of step 1, triethylamine (324 mg, 0.45 mL, 3.21 mmol) and (2,4- dimethoxyphenyl)methanamine (195 mg, 0.18 mL, 1.17 mmol) in CH2CI2 at 0 C (2.5 mL), was added TiCl4 (0.64 mL, 1.0 M in CH2C12, 0.64 mmol). The mixture was stirred at 0 C for 15 min. The mixture was brought to room temperature and stirred overnight. The mixture was diluted with CH2CI2 and quenched at 0 C with saturated NaHCC>3 solution. The organic layer was separated using a phase separator cartridge, and the aqueous layer was washed with additional CH2CI2. The CH2CI2 solution was concentrated under reduced pressure. To the residue, diphenyl ether (5.0 mL) and <strong>[1186-73-8]trimethyl methanetricarboxylate</strong> (380 mg, 2.0 mmol) were added. The mixture was stirred at 200 C for 10 min and then cooled. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (0-100% gradient EtOAc in CH2CI2) to afford the title compound as a yellow oil (200 mg, 40%). (2670) LC-MS 598.5 [M+H]+, RT 1.81 min

Reference： [1]Patent: WO2016/109706,2016,A1 .Location in patent: Page/Page column 200

46
[ 20781-20-8 ]
[ 4107-65-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tris(2,2'-bipyridyl)ruthenium dichloride; oxygen; copper diacetate; lithium tert-butoxide; In dimethyl sulfoxide; at 35℃; for 20h;Schlenk technique; Microwave irradiation;	Added to the Schlenk reaction tube 18.1 mg (0.10 mmol) copper acetate, 16.0 mg (0.025 mmol) three (2, 2' - bipyridyl) ruthenous, 16.0 mg (0.02 mmol) tert lithium ethoxide, using Schlenk double-row tube vacuum pumping, access oxygen state, adding 79 uL (0.5 mmol) 2, 4 - dimethoxybenzylamine, 2.5 ml dimethyl sulfoxide, the use of the Schlenk tube with double row sustained and the oxygen to the reaction system, the temperature control of the reaction system 35 C, white light LED lamp (wavelength 400 - 760 nm) irradiation, stirring for 20 hours after the, adding 3 ml saturated sodium acid sulfite aqueous solution and 10 ml ethyl acetate, extraction liquid, anhydrous magnesium sulfate drying, to remove the magnesium sulfate, the resulting organic phase is concentrated, the concentrate with silica gel column chromatography, to obtain 2, 4 - dimethoxy carbonitrile, yield 90%

Reference： [1]Patent: CN107814751,2018,A .Location in patent: Paragraph 0024-0026
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 328 - 332
[3]Angewandte Chemie - International Edition,2016,vol. 55,p. 15802 - 15806
Angew. Chem.,2016,vol. 128,p. 16034 - 16038,5

47
[ 67911-21-1 ]
[ 20781-20-8 ]
3-(2,4-dimethoxybenzyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	In tetrahydrofuran; at 0 - 180℃; for 2h;	[0266] 2,4-Dimethoxy benzylamine (1.45 g, 8.67 mmol) was added dropwise at 0 C to a solution of <strong>[67911-21-1]6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione</strong> (1.21 g, 8.67 mmol) in THF (5 mL). The semi soild mixture was warmed to 90 C to remove the THF and the solid slowly melted as the mixture was warmed to 180 C for 2 h. The solution was cooled to 60 C and poured onto iced DIPE resulting in formation of a gum. This was separated and evaporated to afford the title compound as an orange gum (1.49 g, 59%).
	With dmap; acetic acid; for 8h;Reflux; Inert atmosphere;	To a stirred solution of 10.0 g (71 .4 mmol) of 6,6-dimethyl-3-oxabicyclo[3.1 .0]hexane- 2,4-dione in 150 mL of AcOH was added 1 1 .9 g (71 .4 mmol) of (2,4- dimethoxyphenyl)methylamine and 0.87 g (7.1 mmol) of DMAP at rt. The mixture was heated at reflux for 8 h under Ar atmosphere and cooled to rt. The mixture was concentrated; the residue was diluted with 200 mL of saturated NaHC03, extracted with three 30 mL portions of DCM. The combined organic extracts were washed with 50 mL of 1 N HCI, dried over anhydrous Na2S04. After filtration, the filtrate was concentrated to afford a residue, which was purified by silica gel column eluting with 0 to 30 % gradient of EA in PE to afford compound 17-1 . LC-MS: m/e = 290 [M+H]+.

Reference： [1]Patent: WO2016/179554,2016,A1 .Location in patent: Paragraph 0266
[2]Patent: WO2019/94143,2019,A1 .Location in patent: Paragraph 193

48
[ 20781-20-8 ]
[ 96-72-0 ]
2-chloro-N-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14.1 g	With sodium hydrogencarbonate; In dichloromethane;	Intermediate 001 2-Chloro-N-(2,4-dimethox de To a solution of <strong>[96-72-0]2-chloro-5-nitrobenzenesulfonamide</strong> (10.8 g, 42.2 mmol) in dichloromethane (108 mL) was added sodium bicarbonate (7.09 g, 84.4 mmol) and 1-(2,4- dimethoxyphenyl)methanamine (7.05 g, 42.2 mmol). The mixture was stirred overnight. The reaction mixture was concentrated in vacuo, followed by addition of water (75 mL) and ethyl acetate (75 mL). After stirring for 10 min the resulting precipitate was separated by filtration and it was dried at 40C overnight in vacuo to yield 2-chloro-N-(2,4- dimethoxybenzyl)-5-nitrobenzenesulfonamide (14.1 g, 36.5 mmol, 86 % yield). LC-MS (Method A): Rt = 1.17 min MS (ESIneg): m/z = 385 (M-H)+ 1H-NMR (400MHz, DMSO-d6) [ppm]: 3.56 (s, 3H), 3.61 (s, 3H), 4.08 (s, 2H), 6.10 (d, 1H), 6.26 (dd, 1H), 7.04 (d, 1H), 7.79 (d, 1H), 8.19 (d, 1H), 8.28 (dd, 1H), 8.45 (s, 1H).

Reference： [1]Patent: WO2016/198374,2016,A1 .Location in patent: Page/Page column 87

49
[ 21279-62-9 ]
[ 20781-20-8 ]
3-[(2,4-dimethoxybenzyl)amino]pyrazine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With pyridine; In methanol; at 140℃; for 0.5h;Sealed tube; Microwave irradiation;	General procedure: Compounds 1-6 were prepared according to conventional organic synthesis methods. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was dissolved in THF (20 mL) in a round bottom flask and after that treated with two equivalents of the corresponding benzylamine and an equimolar amount of triethylamine. The reaction was conducted with continuous stirring and heating (70 C) under reflux in an oil bath for 15 h. Compounds 7-15 were synthesised using a microwave reactor with a focused field. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was put into a thick-walled tube together with the corresponding benzylamine (2.54 mmol), pyridine (1.27 mmol), methanol (approx. 5 mL) and a magnetic stir bar and then sealed with a special cap. The reaction parameters were set according to the previously published paper as follows-140 C, 30 min, 200 W [29]. Reaction progress was checked by TLC (hexane:ethyl acetate-1:1). Regardless of the synthesis method used,all reaction mixtures were adsorbed on silica and subjected to preparative flash chromatography (hexane and ethyl acetate, gradient elution, detection wavelengths 260 nm and 280 nm). Products were recrystallized from ethanol or ethanol and water if necessary. All final substances were chemically characterized (1H-NMR, 13C-NMR, IR, melting point and elemental analysis).

Reference： [1]Molecules,2017,vol. 22

50
[ 1186647-69-7 ]
[ 20781-20-8 ]
N-[(2,4-dimethoxyphenyl)methyl]-3-iodo-1H-pyrazolo[4.3-c]pyridin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In dimethyl sulfoxide; at 120℃; for 3h;	To a solution of 4-chloro-3-iodo-lH-pyrazolo[4,3-c]pyridine (8.5 g, 30 mmol) in DMSO (100 mL) was added (2,4-dimethoxyphenyl)methanamine (15.3 g, 90 mmol). The mixture was heated at 120 C for 3 h. The mixture was diluted EtOAc (200mL), washed with water and brine, dried over Na2S04, concentrated to afford N-(2,4-dimethoxybenzyl)-3-iodo- lH-pyrazolo[4,3-c]pyridin-4-amine (8.6 g, 70%) as a yellow oil which was used for next step without further purification.
67%	In dimethyl sulfoxide; at 120℃;Inert atmosphere;	A solution of 4-chloro-3-iodo-lH-pyrazolo[4,3-c]pyridine (1.10 g, 3.74 mmol, 1.00 eq) and (2,4- dimethoxyphenyl)methanamine (1.97 g, 1 1.2 mmol, 3.0 eq) in DMSO (20 mL) was stirred O/N at l20C under nitrogen atmosphere. The reaction mixture was then diluted with water (30 mL) and extracted with DCM (2x30mL). Combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica (DCM:MeOH, gradient 100: 1 to 10: 1) afforded the title compound as a brown solid (1.3 g, 67%). LC/MS: 410.9 [M+H]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1496 - 1507
[2]Patent: WO2016/210165,2016,A1 .Location in patent: Page/Page column 67-68
[3]Patent: WO2019/192962,2019,A1 .Location in patent: Paragraph 00189

51
[ 3364-80-5 ]
[ 20781-20-8 ]
[ 79341-69-8 ]
[ 106-95-6 ]
3-(allyloxy)-1-(2,4-dimethoxybenzyl)-4-phenyl-5-(thiazol-4-yl)-1,5-dihydro-2H-pyrrol-2-one [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2961 - 2964

52
[ 2460-58-4 ]
[ 20781-20-8 ]
2-(((2,4-dimethoxybenzyl)amino)methyl)-5-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.3%		The compound <strong>[2460-58-4]2-hydroxy-4-nitrobenzaldehyde</strong> (4 g, 23.9 mmol) was dissolved in methanol (100 mL)2,4-dimethoxybenzylamine (4.8 g, 28.7 mmol) and acetic acid (1.44 g, 23.9 mmol) were added.After reaction at room temperature for 0.5 h,Sodium cyanoborohydride (3 g, 47.8 mmol) was added in portions,Continue to react 2h,After the addition of dichloromethane,Washed with saturated sodium bicarbonate and saturated brine,Dry concentrated,Crude beating (dichloromethane / petroleum ether = 1: 10)The yield of 2 - (((2,4-dimethoxybenzyl) ammonia) methyl) -5-nitrophenol (6.5 g) was 85.3percent.

Reference： [1]Patent: CN106349233,2017,A .Location in patent: Paragraph 0173; 0174; 0175; 0176

53
[ 4653-08-1 ]
[ 20781-20-8 ]
N-(2,4-dimethoxybenzyl)-4-oxo-4-(thiophen-2-yl)butanamide [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 4779 - 4782

54
[ 20781-20-8 ]
[ 82671-02-1 ]
2-chloro-6-((2,4-dimethoxybenzyl)amino)-5-fluoronicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; at 20℃; for 2h;	(0927) [00328] Into a 250-mL round-bottom flask was added 2,6-dichloro-5-fluoropyridine-3- carbonitrile (5.00 g, 26.2 mmol), (2,5-dimethoxyphenyl)methanamine (13.0 g, 77,8 mmol), and ethanol (100 mL). The solution was stirred for 2 h at RT. The resulting solids were collected by filtration and dried in vacuo to afford the title compound as a white solid (6.6 g, 78%). LCMS (ESI, m/z): 322 \| 1

Reference： [1]Patent: WO2017/139778,2017,A1 .Location in patent: Paragraph 00328

55
[ 20781-20-8 ]
[ 70049-46-6 ]
2-chloro-N-(2,4-dimethoxybenzyl)-6-methoxyquinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dimethyl sulfoxide; at 90℃; for 48h;	To a mixture of 2,4- dichloro-<strong>[70049-46-6]6-methoxyquinoline</strong> (6.0 g, 26.3 mmol) and (2,4-dimethoxyphenyl)methanamine (6.60 g, 39.5 mmol) in DMSO (80 ml) was added Et3N (11.00 ml, 79 mmol). The reaction mixture was stirred at 90 °C for 48 h. Then the reaction was cooled to 20 °C, and dilutedwith EtOAc (100 mL) and water (100 mL). The aqueous layer was extracted with EtOAc (3 x 100 mL). The combined organic layers were dried over Na2504, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (5i02, PE:EtOAc =10:1 to 1:1) to give the title compound.

Reference： [1]Patent: WO2017/155765,2017,A1 .Location in patent: Page/Page column 68

56
[ 20781-20-8 ]
[ 41103-17-7 ]
C₁₆H₁₉N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 3h;	To a solution of 53 (500 mg, 2.68 rnmol) in DMF is added potassium carbonate (555 mg. 4.02 nimol) and 2,4-diniethoxybenzylarnine (500 mg, 2.99 mrnol). After stirring al 50 C for 3 hours, the mixture is cooled, diluted with FA, and washed with saturated aqueous lithium chloride solution (20 mL 3). The organic layer is dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column chromatography to give 54 as a solid, (617 mg, 73%). (MS: [M+T-W 3181)

Reference： [1]Patent: WO2017/176812,2017,A1 .Location in patent: Paragraph 0283

57
[ 50-00-0 ]
[ 1198-14-7 ]
[ 20781-20-8 ]
5-bromo-7-(((2,4-dimethoxybenzyl)amino)methyl)quinolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%		The solution of 2,4-dimethoxybenzylamine (248 mu, 0.276 g, 1.65 mmol) in ethanol (4 mL) was added 37percent formaldehyde (62 mu, 0.049 g, 1.65 mmol). The mixture was stirred for 1 hour. Then the solution of <strong>[1198-14-7]5-bromoquinolin-8-ol</strong> (0.336 g, 1.5 mmol) in ethanol (5 mL) was added to the reaction mixture. After that the mixture was refluxed at 50°C for 56 hours. The reaction mixture was allowed to cool down and the obtained precipitate was filtered off, washed with ethanol and crystallized from ethanol to give the titled compound (0.170 g, 28percent) as yellow crystals. Mp. 146-148 °C. 1 H NMR (300 MHz, CDCI3): delta 3.80-3.82 (d, 8H), 4.07(s, 2H), 6.44 (d, 2H), 7.08 (d, 1 H), 7.46-7.51 (m, 1 H), 7.62 (s, 1 H), 8.46 (d, 1 H), 8.89 (s, 1 H). 13C NMR (75 MHz, CDCI3): delta 47.7, 49.5, 55.2, 55.3, 98.6, 103.7, 109.1 , 118.8, 120.6, 122.1 , 127.0, 130.9, 131.0, 135.2, 140.0, 149.0, 153.1 , 158.7, 160.5. LCMS RT= 4.12 min. ESI+ m/z: 403.5 [M+H+].

Reference： [1]Patent: WO2017/175018,2017,A2 .Location in patent: Page/Page column 46; 48; 49

58
[ 20781-20-8 ]
[ 112811-71-9 ]
1-cyclopropyl-7-(2,4-dimethoxybenzylamino)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; N,N-dimethyl-formamide; at 120℃; for 6h;	A three-necked flask was charged with 100 g of <strong>[112811-71-9]1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate ethyl ester</strong>,Then add 600mL DMF: DMS0 = 1: 1 mixed solvent, stirred, was added 2,4-dimethoxybenzylamine 54mL, heated to 120 C for 6h, cooled,The reaction solution was poured into 1mol / L dilute hydrochloric acid, stirred, added 500mLEA extraction, the organic layer was separated, the aqueous phase was extracted with EA300mLX2,The combined organic layers were dried and evaporated to dryness to give 92.3 g of the yellow product which was used in the next step without further purification.

Reference： [1]Patent: CN104292158,2017,B .Location in patent: Paragraph 0050-0052

59
[ 50-00-0 ]
[ 88333-03-3 ]
[ 20781-20-8 ]
[ 612-20-4 ]
C₂₆H₂₈N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.5%	In methanol;Inert atmosphere; Reflux; Green chemistry;	General procedure: The oxocomponent(i.e. the aldehyde or the ketone) (0.5 mmol, 1 eq.), the amine (0.5 mmol, 1 eq.), theisocyanide (0.5 mmol, 1 eq.), and <strong>[612-20-4]2-hydroxymethylbenzoic acid</strong> (0.5 mmol, 1 eq.) were one-potmixed in methanol (2 M, 250 muL) and stirred at reflux temperature under a nitrogen atmosphere for3-4h. The formation of the Ugi alpha-acylamino amide was monitored by TLC, and the crude reactionmixture was evaporated and filtered through a pad of silica gel (n-hexane/ EtOAc). The Ugi alpha-acylamino amide (0.15 mmol) was then stirred for 10 minutes at room temperature in 4N HClsolution in 1,4-dioxan (1 mL). The reaction was then evaporated to dryness and triturated with nhexaneto give the hydrochloride salt of the corresponding N,N?-substituted alpha-amino amide.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 1196 - 1199

60
[ 931-53-3 ]
[ 20781-20-8 ]
[ 612-20-4 ]
[ 620-23-5 ]
C₃₂H₃₈N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In methanol;Inert atmosphere; Reflux; Green chemistry;	General procedure: The oxocomponent(i.e. the aldehyde or the ketone) (0.5 mmol, 1 eq.), the amine (0.5 mmol, 1 eq.), theisocyanide (0.5 mmol, 1 eq.), and <strong>[612-20-4]2-hydroxymethylbenzoic acid</strong> (0.5 mmol, 1 eq.) were one-potmixed in methanol (2 M, 250 muL) and stirred at reflux temperature under a nitrogen atmosphere for3-4h. The formation of the Ugi alpha-acylamino amide was monitored by TLC, and the crude reactionmixture was evaporated and filtered through a pad of silica gel (n-hexane/ EtOAc). The Ugi alpha-acylamino amide (0.15 mmol) was then stirred for 10 minutes at room temperature in 4N HClsolution in 1,4-dioxan (1 mL). The reaction was then evaporated to dryness and triturated with nhexaneto give the hydrochloride salt of the corresponding N,N?-substituted alpha-amino amide.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 1196 - 1199

61
[ 20781-20-8 ]
[ 637301-19-0 ]
tert-butyl 8-(2,4-dimethoxybenzylamino)-3-azabicyclo[3.2.1]octane-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.5%	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 25℃; for 2h;	Tert-butyl 8-oxo-3-azabicyclo[3.2.1]octane-3-carboxylate (0.8 g, 3.55 mmol) and (2,4-dimethoxyphenyl)methylamine (0.6 g, 3.59 mmol) was dissolved in dichloromethane (10 mL), acetic acid (20 muL) and sodium triacetyloxyborohydrate (2 g, 9.44 mmol) were added, stirred and reacted at 25 C for 2 h. The reaction solution was quenched with water (10 mL), the phases were separated, extracted with dichloromethane (20 mL*3), and the organic phases were combined, dried over anhydrous sodium sulfate, filtrated, concentrated. The crude product was separated and purified by silica gel column chromatography (petroleum ether : ethyl acetate =3:1) to obtain the title compound as colorless oil (0.8 g, yield 61.5 %).

Reference： [1]Patent: EP3281942,2018,A1 .Location in patent: Paragraph 0196; 0197

62
[ 13726-16-4 ]
[ 20781-20-8 ]
C₁₇H₁₈ClNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20 - 25℃; for 24h;Inert atmosphere;	5) 3-(tert-butyl)-N-(4-chloro-3-methoxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (200 mg, 1.17 mmol, 1.0 eq) in toluene (20 mL) was added 2,4-dimethoxybenzyl amine (215 mg, 1.29 mmol, 1.1 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (30 mL) and then NaBH4 (87 mg, 2.34 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (1.17 mmol, 1.0 eq) in DMF (10 mL) was added the acid (234 mg, 1.29 mmol, 1.1 eq), DIEA (755 mg, 5.85 mmol, 5 eq) and HBTU (532 mg, 1.40 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (200 mL) and washed with 10percent aqHCl (150 mL), sat NaHCO3 (150 mL) and water (4*50 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25percent to 75percent)) to give the amide, which was directly used in the next step. The amide was treated with 95percent TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10percent to 50percent) to give the desired product in 37percent (147 mg, >95percent purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C17H23ClN3O2: 336.0 (M+H), Found 336.0.

Reference： [1]Patent: US2018/118679,2018,A1 .Location in patent: Paragraph 0221-0222

63
[ 20781-20-8 ]
[ 103438-86-4 ]
C₁₆H₁₆FNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20 - 25℃; for 24h;Inert atmosphere;	10) 3-cyclopropyl-N-(3-(cyclopropylmethoxy)-2-fluorobenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (1.0 g, 7.14 mmol, 1.0 eq) in toluene (20 mL) was added 2,4-dimethoxybenzyl amine (1.2 g, 7.14 mmol, 1.0 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (25 mL) and then NaBH4 (540 mg, 14.28 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (7.14 mmol, 1.0 eq) in DMF (10 mL) was added the acid (1.20 g, 7.14 mmol, 1.0 eq), DIEA (4.61 g, 35.72 mmol, 5 eq) and HBTU (3.25 g, 8.57 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aqHCl (130 mL), sat NaHCO3 (130 mL) and water (430 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was taken in 25 mL of methanol and NaOH (286 mg, 7.14 mmol, 1.0 eq) was added and stirred at room temperature for 24 h. Methanol was removed and the residue was neutralized with 10% aq HCl. The reaction mixture was then extracted with ethyl acetate (2). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane) to give the amide. To a solution of the hydroxy amide (360 m g, 0.82 mmol, 1.0 eq) in DMF (10 mL) was added Cs2CO3 (1.34 g, 615 mmol, 2.0 eq) and stirred at room temperature for 20 min. Then bromide (221 mg, 1.64 mmol, 2 eq) was added and stirred at rt for 24 h. The reaction mixture was then diluted with Ethyl acetate (25 mL) and washed with water (4*). Organic layer was collected, dried (MgSO4) and evaporated to give a residue, which was then treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product (22 mg, >95% purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C19H22CFN3O2: 344.0 (M+H), Found 344.0.

Reference： [1]Patent: US2018/118679,2018,A1 .Location in patent: Paragraph 0231-0233

64
[ 20781-20-8 ]
[ 108373-05-3 ]
C₁₈H₂₂BrNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20 - 25℃; for 24.0h;Inert atmosphere;	17) N-(3-bromo-4-ethoxybenzyl)-3-isopropyl-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (1.0 g, 437 mmol, 1.0 eq) in toluene (25 mL) was added 2,4-dimethoxybenzyl amine (802 mg, 4.80 mmol, 1.1 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (25 mL) and then NaBH4 (330 mg, 8.74 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (1.46 mmol, 1.0 eq) in DMF (15 mL) was added the acid (244 mg, 1.46 mmol, 1.0 eq), DIEA (939 mg, 1.30 mmol, 5 eq) and HBTU (662 mg, 1.75 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aqHCl (120 mL), sat NaHCO3 (120 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C17H23BrN3O2: 380.0 (M+H), Found 380.0.

Reference： [1]Patent: US2018/118679,2018,A1 .Location in patent: Paragraph 0248-0249

65
[ 20781-20-8 ]
[ 108373-05-3 ]
C₁₈H₂₀BrNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20 - 25℃; for 24.0h;Inert atmosphere;	16) N-(3-bromo-4-ethoxybenzyl)-3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (1.0 g, 437 mmol, 1.0 eq) in toluene (25 mL) was added 2,4-dimethoxybenzyl amine (802 mg, 4.80 mmol, 1.1 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (25 mL) and then NaBH4 (330 mg, 8.74 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (1.46 mmol, 1.0 eq) in DMF (15 mL) was added the acid (263 mg, 1.46 mmol, 1.0 eq), DIEA (939 mg, 1.30 mmol, 5 eq) and HBTU (662 mg, 1.75 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with Ethyl acetate (20 mL) and washed with 10% aqHCl (120 mL), sat NaHCO3 (120 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H25BrN3O2: 394.0 (M+H), Found 394.0.

Reference： [1]Patent: US2018/118679,2018,A1 .Location in patent: Paragraph 0246-0247

66
[ 20781-20-8 ]
[ 147624-13-3 ]
C₁₇H₁₈FNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20 - 25℃; for 24h;Inert atmosphere;	19) 3-cyclopropyl-N-(3-fluoro-2-methylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (500 mg, 3.62 mmol, 1.0 eq) in toluene (15 mL) was added 2,4-dimethoxybenzyl amine (605 mg, 3.62 mmol, 1.0 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (15 mL) and then NaBH4 (274 mg, 7.24 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (3.62 mmol, 1.0 eq) in DMF (15 mL) was added the acid (600 mg, 3.62 mmol, 1.0 eq), DIEA (2.33 g, 18.1 mmol, 5 eq) and HBTU (1.65 g, 4.34 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aqHCl (120 mL), sat NaHCO3 (120 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product (282 mg, >95% purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H19FN3O: 288.0 (M+H), Found 288.0.

Reference： [1]Patent: US2018/118679,2018,A1 .Location in patent: Paragraph 0252-0253

67
[ 56724-03-9 ]
[ 20781-20-8 ]
C₁₈H₂₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20 - 25℃; for 24h;Inert atmosphere;	28) 3-cyclopropyl-N-(3-methoxy-2-methylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (1.0 g, 6.66 mmol, 1.0 eq) in toluene (20 mL) was added 2,4-dimethoxybenzyl amine (1.23 g, 7.33 mmol, 1.1 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (25 mL) and then NaBH4 (506 mg, 13.32 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (4.44 mmol, 1.0 eq) in DMF (15 mL) was added the acid (737 mg, 4.44 mmol, 1.0 eq), DIEA (2.86 g, 22.2 mmol, 5 eq) and HBTU (2.02 g, 5.38 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aqHCl (120 mL), sat NaHCO3 (120 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product (80 mg, >95% purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C17H22N3O2: 300.0 (M+H), Found 300.0.

Reference： [1]Patent: US2018/118679,2018,A1 .Location in patent: Paragraph 0269-0270

68
[ 24973-22-6 ]
[ 20781-20-8 ]
C₁₈H₂₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20 - 25℃; for 24h;Inert atmosphere;	27) 3-(tert-butyl)-N-(3-methoxy-4-methylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of 3-Methoxy-3-methyl-benzaldehyde (250 mg, 1.66 mmol, 1.0 eq) in toluene (20 mL) was added 2,4-dimethoxybenzyl amine (306 mg, 1.83 mmol, 1.1 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (20 mL) and then NaBH4 (129 mg, 3.32 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (1.66 mmol, 1.0 eq) in DMF (20 mL) were added the acid (333 mg, 1.83 mmol, 1.1 eq), DIEA (1.07 g, 8.32 mmol, 5 eq) and HBTU (757 g, 1.99 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (75 mL) and washed with 10% aqHCl (150 mL), sat NaHCO3 (150 mL) and water (4*50 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product in (263 mg, >95% purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H26N3O2: 316.0 (M+H), Found 316.0.

Reference： [1]Patent: US2018/118679,2018,A1 .Location in patent: Paragraph 0267-0268

69
[ 13479-88-4 ]
[ 20781-20-8 ]
5-chloro-N-(2,4-dimethoxybenzyl)thiazolo[5,4-d]pyrimidin-7-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20℃; for 3.0h;	A mixture of compound 21 (1.00 g, 4.85 mmol), dimethoxybenzylamine (1.06 g, 6.31 mmol) and DIPEA (1.27 mL, 7.28 mmol) in DMSO (13 mL) was stirred at rt for 3 h. The mixture was poured into water (55 mL), cooled at 0C for 20 mm and then filtered. The solid obtained was washed with water. The product was then dried in vacuo. Crude product was purified by silica-gel column chromatography and isolated as a light yellow solid. ?H NMR (500 MHz, CDC13) oe 8.66 (s, 1H), 7.30 (d, J = 8.1 Hz, 1H), 6.81 (s, 1H), 6.44 (d, J = 10.7 Hz, 2H), 4.73 (d, J = 5.8 Hz, 2H), 3.84 (s, 3H), 3.80 (s, 3H). ?3C NMR (126 MHz, CDC13) oe 161.9, 160.9, 158.8, 156.9, 156.3,150.6, 131.0, 130.1, 117.7, 104.0, 98.7, 55.49, 55.46, 40.5. MS [ESIi m/z: 337.15 and339.14 [M+Hj

Reference： [1]Patent: WO2018/137036,2018,A1 .Location in patent: Paragraph 00230

70
[ 2382-10-7 ]
[ 20781-20-8 ]
2-chloro-N-(2,4-dimethoxybenzyl)-9-methyl-9H-purin-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 22℃; for 6h;	A solution of compound 29 (1.21 g, 5.96 mmol) in DMSO (15 mL) and 2,4-dimethoxybenzylamine (1.16 mL, 7.74 mmol) was added DIPEA (1.78 mL, 8.91 mmol) at room temperature and stirred at 6 h at the same temperature. To the reaction mixture was added H20 (20 mL) and shaken well, a white precipitate was observed. Cooled the mixture at 0 C for 20 mm filtered through the filter paper and the solid was washed with water (3x). The precipitate was dried to obtain 30 (1.79 g, 90%) as a white solid.?H-NMR (400 MHz, CD3OD) oe 7.97 (s, 1H), 7.25 (d, J 8.2 Hz, 1H), 6.55 (d, J 2.3 Hz, 1H), 6.51-6.39 (m, 1H), 4.65 (s, 2H), 3.85 (s, 3H), 3.77 (s, 3H), 3.75 (s, 3H); LCMS (m/z) [M+Hj 333.24.

Reference： [1]Patent: WO2018/137036,2018,A1 .Location in patent: Paragraph 00232; 00233

71
[ 873975-41-8 ]
[ 50-00-0 ]
[ 20781-20-8 ]
[ 33578-00-6 ]
N-(2-((2-azidoethyl)amino)-2-oxoethyl)-N-(2,4-dimethoxybenzyl)-2-ethynylbenzamide [ No CAS ]