[ CAS No. 60853-81-8 ]

Name: 60853-81-8|2-(Dimethylamino)acetyl chloride hydrochloride|95%
Brand: Ambeed
SKU: A689408
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Quality Control of [ 60853-81-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 60853-81-8 ]

Product Details of [ 60853-81-8 ]

CAS No. :	60853-81-8	MDL No. :	MFCD02094025
Formula :	C₄H₉Cl₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MVAXDKDOPWPFML-UHFFFAOYSA-N
M.W :	158.03	Pubchem ID :	13994991
Synonyms :

Calculated chemistry of [ 60853-81-8 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.2
TPSA :	20.31 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) :	-6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.64
Log Po/w (WLOGP) :	1.12
Log Po/w (MLOGP) :	0.46
Log Po/w (SILICOS-IT) :	0.18
Consensus Log Po/w :	0.68

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.72
Solubility :	3.0 mg/ml ; 0.019 mol/l
Class :	Very soluble
Log S (Ali) :	-1.68
Solubility :	3.31 mg/ml ; 0.0209 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.91
Solubility :	19.3 mg/ml ; 0.122 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 60853-81-8 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P260-P264-P270-P280-P301+P310+P330+P331-P303+P361+P353+P310-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501	UN#:	2923
Hazard Statements:	H301-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 60853-81-8 ]

* 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 [ 60853-81-8 ]
Downstream synthetic route of [ 60853-81-8 ]

[ 60853-81-8 ] Synthesis Path-Upstream 1~2

1
[ 1118-68-9 ]
[ 60853-81-8 ]

Reference： [1] Farmaco, Edizione Scientifica, 1986, vol. 41, # 2, p. 131 - 150
[2] Patent: US2003/212111, 2003, A1,
[3] RSC Advances, 2017, vol. 7, # 75, p. 47297 - 47308
[4] Patent: CN108707139, 2018, A, . Location in patent: Paragraph 0437; 0440; 0441; 0442

2
[ 2491-06-7 ]
[ 60853-81-8 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 184 - 188
[2] Archiv der Pharmazie, 1991, vol. 324, # 7, p. 433 - 437
[3] Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 7, p. 969 - 972

[ 60853-81-8 ] Synthesis Path-Downstream 1~69

1
[ 1118-68-9 ]
[ 60853-81-8 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;	EXAMPLE 125 Preparation of N-{3-[3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]phenyl}-2-dimethylaminoacetamide To a 25 mL flask was added N,N-dimethylglycine (500 mg, 4.85 mmol) and thionyl chloride (5 mL). The resulting solution was allowed to stir at ambient temperature under N2 for 3 h. The excess thionyl chloride was removed in vacuo to provide N,N-dimethylaminoacetyl chloride hydrochloride as a white powder.
	With oxalyl dichloride; N,N-dimethyl-formamide; In acetonitrile; at 30℃; for 3h;Inert atmosphere;	N,N-dimethylglycine (1 g, 10 mmol), acetonitrile was added to a 100 mL three-necked flask under argon(15 mL) and DMF (5d), oxalyl chloride (1.23 g, 10 mmol) was added dropwise at room temperature.The oil bath was heated to 30 C for 3 h. Cool down to room temperature.The reaction solution was used in the next step without treatment.

Reference： [1]Farmaco, Edizione Scientifica,1986,vol. 41,p. 131 - 150
[2]Patent: US2003/212111,2003,A1
[3]RSC Advances,2017,vol. 7,p. 47297 - 47308
[4]Patent: CN108707139,2018,A .Location in patent: Paragraph 0437; 0440; 0441; 0442

2
[ 2491-06-7 ]
[ 60853-81-8 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 184 - 188
[2]Archiv der Pharmazie,1991,vol. 324,p. 433 - 437
[3]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 969 - 972

3
[ 60853-81-8 ]
[ 135509-39-6 ]
[ 135509-43-2 ]

Reference： [1]Archiv der Pharmazie,1991,vol. 324,p. 433 - 437

4
[ 60853-81-8 ]
(4S,4aS,5aR,12aS)-9-Amino-4-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide; compound with sulfuric acid [ No CAS ]
<4S-(4α,12aα)>-4-(dimethylamino)-9-<<(dimethylamino)acetyl>amino>-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 184 - 188

5
[ 60853-81-8 ]
<4S-(4α,12aα)>-9-amino-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-2-naphthacenecarboxamide monosulfate [ No CAS ]
<4S-(4α,12aα)>-4-(dimethylamino)-9-<<(dimethylamino)acetyl>amino>-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-2-naphthacenecarboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 184 - 188

6
[ 60853-81-8 ]
<4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide disulfate [ No CAS ]
<4S-(4α,12aα)>-4,7-bis(dimethylamino)-9-<<(dimethylamino)acetyl>amino>-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 184 - 188

7
[ 60853-81-8 ]
<4S-(4α,12aα)>-9-amino-7-(diethylamino)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide disulfate [ No CAS ]
<4S-(4α,12aα)>-7-(diethylamino)-4-(dimethylamino)-9-<<(dimethylamino)acetyl>amino>-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 184 - 188

8
[ 60853-81-8 ]
rifampicin-quinone [ No CAS ]
8-N,N-dimethylaminoacetyl-rifampicin-quinone [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1986,vol. 41,p. 131 - 150

9
[ 612501-25-4 ]
[ 60853-81-8 ]
4-(3-chloro-2-fluoroanilino)-6-[(3S)-1-(N,N-dimethylaminoacetyl)piperidin-3-yloxy]-7-methoxyquinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2h;	Example 59; 4-(3-chloro-2-fluoroanilino)-6-[(3S)-1-(N, N-dimethylaminoacetyl) piperidin-3-yloxy]-7" methoxyquinazoline; N, N-Dimethylaminoacetyl chloride hydrochloride (69mg) was added portionwise to a stirred solution of 4- (3-chloro-2-fluoroanilino)-7-methoxy-6- [ (3S)-piperidin-3- yloxy] quinazoline hydrochloride (175 mg; prepared as described in Example 49) and diisopropylethylamine (210 Ll) in methylene chloride (25ml) at 0C. The reaction mixture was allowed to stir for 2 hours to room temperature. The reaction mixture was washed with saturated sodium bicarbonate solution, dried (MgS04), filtered and evaporated to a foam. This was purified by column chromatography eluting with increasingly polar mixtures of methylene chloride/methanol (saturated with ammonia) (100/0 to 90/10). The fractions containing the desired product were combined and evaporated under vacuum to give the title product as a white foam (0.152g, 78%) ; 1H NMR Spectrum: (DMSO d6 at 100 C) 1.40-1. 65 (m, 1H) ; 1.75-1. 95 (m, 2H); 2.00-2. 30 (m, 7H); 3.05 (dd, 2H) ; 3.40-3. 62 (m, 2H) ; 3. 62-3.75 (m, 1H) ; 3.88 (dd, 1H) ; 3.95 (s, 3H) ; 4.45-4. 65 (m, 1H); 7.15-7. 30 (m, 2H) ; 7.30-7. 47 (m, 1H) ; 7.50-7. 7 (m, 1H); 7.88 (s, 1H) ; 8.40 (s, 1H) ; 9.25 (s, 1H) ; Mass Spectrum: (M+H)+ 488.

Reference： [1]Patent: WO2003/82831,2003,A1 .Location in patent: Page/Page column 153

10
3-endo-{8-[2-(cyclohexylmethylamino)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}benzamide bis(trifluoroacetate) [ No CAS ]
[ 60853-81-8 ]
3-endo-(8-{2-[cyclohexylmethyl-(2-dimethylamino-acetyl)amino]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-benzamide bis(trifluoroacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of the product of the previous step (33.0 mg, 0.055 mmol) in DCM (0.3 mL) at ambient temperature was added DIPEA (28.4 mg, 0.22 mmol) followed by dimethylamino-acetyl chloride HCl salt (12.6 mg, 0.08 mmol). The reaction mixture was stirred for 10 min and then concentrated. The resulting residue was dissolved in 50% acetic acid in water (1.5 mL), filtered and purified by reverse phase preparative HPLC to give the bis TFA salt of the title compound.(16.1 mg). (m/z): [M+H]+ calcd for C27H42N4O2 455.33; found 455.2.

Reference： [1]Patent: US2007/219278,2007,A1 .Location in patent: Page/Page column 40

11
[ 1001017-53-3 ]
[ 60853-81-8 ]
methyl (4-[[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl](N,N-dimethylglycyl)amino]methyl}phenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile; at 20℃; for 10h;	Example 2; Methyl (4-{ [ [3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl] (lambdayV- dimethylglycyl)amino]methyl}phenyl)acetate; sThe product of example 1, step (ix) (200mg) was suspended in MeCN. AzetaN-dimethylglycyl chloride hydrochloride (1 lOmg) and triethylamine (0.19ml) were added and the mixture stirred at rt for 1Oh. The mixture was purified by RPetaPLC. Yield lOOmg. 1H nuMR delta (DMSO-de) 7.07 - 7.22 (4H, m), 6.43 (2H, brs), 4.55 (2H, s), 4.13 (2H, t), 3.63 - 0 3.69 (4H, m), 3.60 (3H, s), 3.29 (2H3 m), 3.01 (2H, s), 2.14 (2H, s), 1.31 - 1.97 (6H, in), 0.90 (3H, t). MS: APCI (+ve): 528 (M+H).

Reference： [1]Patent: WO2008/4948,2008,A1 .Location in patent: Page/Page column 37

12
4-amino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrole-2-carboxamide hydrochloride [ No CAS ]
[ 60853-81-8 ]
4-(2-Dimethylaminoacetylamino)-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 16h;	To 0.15 g (0.328 mmol) of 4-amino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrole-2-carboxamide hydrochloride dissolved in 4.5 cm3 of tetrahydrofuran are added, at a temperature in the region of 20 C. under an argon atmosphere, 0.052 g of dimethylaminoacetyl chloride hydrochloride, 0.091 cm3 of triethylamine and 8 mg of 4-dimethylaminopyridine. After stirring for 16 hours at a temperature in the region of 20 C., the reaction mixture is diluted with 15 cm3 of dichloromethane and then washed with twice 10 cm3 of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 148 mg of a beige-coloured solid, which is purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (82/9/9 by volume)]. After concentrating the fractions under reduced pressure, 0.107 g of 4-(2-dimethylaminoacetylamino)-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrole-2-carboxamide is obtained in the form of a yellow solid melting at 178 C.; ES+: m/z=507: [M+H]+. 1H NMR (400 MHz, DMSO d6, delta in ppm) 2.14 (s, 6H); 2.91 (s, 2H); 5.79 (broad m, 1H); 7.06 (broad m, 1H); from 7.25 to 7.31 (m, 3H); 7.39 (m, 1H); 7.50 (m, 1H); 7.58 (d, J=8.5 Hz, 2H); 8.61 (m, 1H); 8.68 (s, 1H); 9.11 (broad s, 1H); 9.49 (broad s, 1H); 11.35 (broad s, 1H);

Reference： [1]Patent: US2008/45542,2008,A1 .Location in patent: Page/Page column 16

13
4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)amide trifluoroacetic acid salt [ No CAS ]
[ 60853-81-8 ]
[ 885692-52-4 ]
4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(2-methylamino-acetyl)-piperidin-4-yl]-phenyl}-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2.66667h;	Example 38 4-Cyano-1H-imidazole-2-carboxylic acid{2-cyclohex-1-enyl-4-[1-(2-dimethylamino-acetyl)-piperidin-4-yl]-phenyl}-amide A mixture of 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt (as prepared in Example 14, step (b), 655 mg, 1.30 mmol) in DCM (15 mL) was cooled to 0 C. and DIEA (0.92 mL, 5.2 mmol) was added. Dimethylaminoacetyl chloride hydrochloride (211 mg, 1.3 mol) was then added portion wise over 10 min. The reaction mixture was stirred at 0 C. for 30 min and allowed to warm to RT and stirred for 2 h. Solvent was removed in vacuo and the resulting residue was partitioned between brine and DCM. The organic layer was separated, dried (Na2SO4) and concentrated. The residue obtained was purified on silica (5% MeOH: DCM) to obtain 432 mg (70%) of the title compound as a white solid. 1H-NMR (CDCl3; 400 MHz): delta 9.49 (s, 1H), 8.24 (d, 1H, J=2.3 Hz), 7.70 (s, 1H), 7.12 (dd, 1H, J=8.4, 2.1 Hz), 7.01 (s, 1H), 5.82 (m, 1H), 4.75 (d, 1H, J=13.4 Hz), 4.13 (d, 1H, J=13.4 Hz), 3.57 (d, 1H, J=14.2 Hz), 3.18 (d, 1H, J=14.2 Hz), 3.12 (td, 1H, J=13.3, 2.4 Hz), 2.73 (dddd, 1H, J=11.9, 11.9, 3.8, 3.8 Hz), 2.65 (ddd, 1H, J=13.3, 13.3, 2.4 Hz), 2.40 (s, 6H), 2.18-2.32 (m, 4H), 1.60-1.98 (m, 8H). Mass spectrum (ESI, m/z): Calcd. for C26H32N6O2, 461.3 (M+H). found 461.2. Example 38b 4-Cyano-1H-imidazole-2-carboxylic acid{2-cyclohex-1-enyl-4-[1-(2-methylamino-acetyl)-piperidin-4-yl]-phenyl}-amide HPLC purification of Example 38a also afforded a small amount of 4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(2-methylamino-acetyl)-piperidin-4-yl]-phenyl}-amide. 1H-NMR (CD3OD; 400 MHz): delta 8.02 (d, 1H, J=8.4 Hz), 7.92 (s, 1H), 7.07 (dd, 1H, J=8.4 Hz, J=2.4 Hz), 6.98 (d, 1H, J=2.4 Hz), 5.73-5.68 (m, 1H), 4.60-4.51 (m, 1H), 3.76-3.68 (m, 1H), 3.20-3.11 (m, 1H), 2.81-2.70 (m, 2H), 2.67 (s, 3H), 2.22-2.13 (m, 4H), 1.88-1.66 (m, 6H), 1.66-1.46 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C25H30N6O2, 447.2 (M+H). found 447.3.

Reference： [1]Patent: US2008/51402,2008,A1 .Location in patent: Page/Page column 54-55

14
[ 60853-81-8 ]
[ 55052-27-2 ]
1-(6-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-dimethylamino-ethanone [ No CAS ]

Reference： [1]Patent: EP1178045,2002,A1 .Location in patent: Page 10

15
4-(5-chloro-2,3-methylenedioxypyrid-4-ylamino)-5-isopropoxy-7-(2-piperazin-1-ylethoxy)quinazoline [ No CAS ]
[ 60853-81-8 ]
[ 692053-82-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃; for 18h;	4- (5-Chloro-2, 3-methylenedioxypyrid-4-ylamino)-5-isopropoxy-7- (2-piperazin- 1-ylethoxy) quinazoline (0.2 g) was added to a stirred mixture of 2-dimethylaminoacetyl chloride hydrochloride (0.097 g), triethylamine (0.15 ml) and methylene chloride (5 ml) that had been cooled to 0C. The reaction mixture was allowed to warm to ambient temperature and stirred for 2 hours. A second portion of each of 2-dimethylaminoacetyl chloride hydrochloride (0.097 g) and triethylamine (0.057 ml) were added and the reaction was stirred at ambient temperature for 16 hours overnight. Methylene chloride (50 ml) was added and the reaction mixture was extracted twice with a saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar solvent mixtures, starting with a 9: 1 mixture of methylene chloride and methanol and ending with a 90: 8: 2 mixture of methylene chloride, methanol and a saturated methanolic ammonia solution. There was thus obtained the title compound as a foam (0.155 g); NMR Spectrum: (CDCl3) 1.55 (d, 6H), 2.3 (s, 6H), 2.6 (m, 4H), 2.9 (t, 2H), 3.1 (s, 2H), 3.65 (m, 4H), 4.25 (t, 2H), 4.85 (s, 1H), 6.15 (s, 2H), 6.55 (s, 1H), 6.85 (s, 1H), 7.75 (s, 1H), 8.6 (s, 1H), 9.6 (s, 1H); Mass Spectrum: M+H+ 572 and 574; Elemental Analysis : Found C, 55.1 ; H, 6.1 ; N, 16.8 ; C27H34CLN705 0.75H20 requires C, 55.4 ; H, 6.1 ; N, 16.7%

Reference： [1]Patent: WO2004/41829,2004,A1 .Location in patent: Page 97

16
[ 319441-55-9 ]
[ 60853-81-8 ]
[ 319442-14-3 ]

Yield	Reaction Conditions	Operation in experiment
11%		2-Dimethylamino-N-(4-(2-thienylcarbonyl)thieno[3,2-d]pyrimidin-2-yl)acetamide hydrochloride (Example 169) A solution of 2-aminothieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (0.15 g, 0.57 mmol) in anhydrous pyridine (6 ML) under argon at 0 C. was treated with N,N-dimethylglycinyl chloride hydrochloride (0.11 g, 0.69 mmol), warmed to room temperature, refluxed for 16 h, cooled, concentrated in vacuo and partitioned between 3-M HCl (25 ML) and EtOAc (25 ML).. The aqueous phase was washed with EtOAc (25 ML), filtered through celite, basified to PH 12 with 10% aqueous sodium hydroxide and the resulting precipitate filtered and dried in vacuo to give a brown solid which was purified by chromatography [SiO2; EtOAc-MeOH (100:0 to 85:15)].. The resulting yellow solid was dissolved in CH2Cl2 (5 ML), treated with 1-M HCl in ether (0.25 ML) and the resulting precipitate filtered and dried in vacuo to give the title compound (32 mg, 11%) as a yellow solid.

Reference： [1]Patent: US6787541,2004,B1 .Location in patent: Page column 88; 109-110

17
[ 60853-81-8 ]
[ 150-13-0 ]
4-(N,N-dimethylamino)acetamidobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydrogencarbonate; In acetonitrile; at 20℃; for 16h;	Example 40; Step 1. 4- (N, N-Dimethylamino) acetamidobenzoic acid (139); [0310] To a solution of N, NDIMETHYLAMINOACETYL CHLORIDE HYDROCHLORIDE (137, LO. LG, 64.2 MMOL) in acetonitrile (300 mL) was added powdered sodium bicarbonate (11. 9g, 141 MMOL) followed by 4- AMINOBENZOIC acid (138,9. 68g, 70.6 MMOL). The mixture was vigorously stirred over 16h at r. t. and acetonitrile was decanted. The remaining gum was triturated with methanol and filtration afforded the title compound 139 (10.9 g, 76% YIELD). H NMR: (400 MHz, DMSO-d6) 8 (PPM) : 10.21 (s, 1H), 7.84 (d, J=8. 4 Hz, 2H), 7.76 (d, J=8.6 Hz, 2H), 4.17 (BS, 2H), 2.27 (s, 6H). LRMS: (m/z): 223.3 (MH+).

Reference： [1]Patent: WO2005/30704,2005,A1 .Location in patent: Page/Page column 190

18
[ 850005-44-6 ]
[ 60853-81-8 ]
(2E)-3-[4-((1Z)-1-{4-[(N,N-dimethylglycyl)oxy]phenyl}-2-phenylbut-1-enyl)phenyl]prop-2-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Prepared from 30 and dimethylaminoacetyl chloride hydrochloride. Yellow solid foam. FOR HNMR and MS data refer to Example 10. Anal. calculated for C29H29N04 1. 31 CF3CO2H : C, 62.78 ; H, 5.05 ; N, 2.32 ; Found: C, 62.80 ; H, 5.25 ; N, 2.41.

Reference： [1]Patent: WO2005/33056,2005,A2 .Location in patent: Page/Page column 55-56

19
N-(3-chloro-2-fluorophenyl)-6-methoxy-7-(piperidin-4-yloxy)quinazolin-4-amine dihydrochloride [ No CAS ]
[ 60853-81-8 ]
N-(3-chloro-2-fluorophenyl)-7-({1-[(dimethylamino)acetyl]piperidin-4-yl} oxy)-6-methoxyquinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2h;	N, N-Dimethylaminoacetyl chloride hydrochloride (100MG) was added portionwise to a stirred solution OF N- (3-CHLORO-2-FLUOROPHENYL)-6-METHOXY-7- (PIPERIDIN-4-YLOXY) QUINAZOLIN- 4-amine dihydrochloride (250mg, 0. 57MMOL) and diisopropylethylamine (300 UL) in methylene chloride (25 ml) at 0C. The reaction mixture was allowed to stir for 2 hours to room temperature. The reaction mixture was washed with saturated sodium bicarbonate solution (25ML), dried (MGS04), filtered and evaporated. The residues were purified by column chromatography eluting with increasingly polar mixtures of methylene chloride/methanol (100/0 to 90/10), followed by methylene chloride/methanol (saturated with ammonia) (90/10). The fractions containing the desired product were combined and evaporated under vacuum to give the title product as a white foam (0.125g, 45%)

Reference： [1]Patent: WO2005/26150,2005,A1 .Location in patent: Page/Page column 94

20
[ 503039-37-0 ]
[ 60853-81-8 ]
[ 866001-26-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium hydrogencarbonate; triethylamine; In acetonitrile; at 20℃; for 24h;	NaHC03 (356mg, 4.24 mmol) was added to a suspension of compound 148 (described in the Patent Application WO 03/024448) (701 mg, 2.12 mmol) and Me2NCH2COCl HCI (670mg, 4.24 mmol) in CH3CN followed by addition of Et3N (295p1, 2.12 mmol). The mixture was stirred at room temperature 24h, concentrated in vacuo and the residue was partitioned between DCM and H20. The aqueous layer was collected, neutralized with NaHCO3 and extracted with fresh DCM, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel affording the title compound 150 (485mg, 55% yield). lH NMR: (DMSO-d6) 8 (ppm) : 9.95 (s, 1H), 8.41 (d, J= 2.0 Hz, 1H), 7.91 (d, J= 8.2 Hz, 2H), 7.79 (d, J= 8.8 Hz, 1H), 7.63 (d, J= 8.2 Hz, 2H), 7.63 (dd, J= 8.8, 2.1 Hz, 1H), 4.71 (s, 2H), 3.84 (s, 3H), 3.11 (s, 2H), 2.30 (s, 6H). m/z: 416.4 (MH+).

Reference： [1]Patent: WO2005/92899,2005,A1 .Location in patent: Page/Page column 113; 115

21
[ 868633-58-3 ]
[ 60853-81-8 ]
(6R,7S,8R)-7-(2-dimethylamino-acetoxy)-6-(2-methoxy-ethoxy)-2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With dmap; triethylamine; In dichloromethane; at 25℃; for 144h;	8. (6R,7S,8R)-7-(2-Dimethylamino-acetoxy)-6-(2-methoxy-ethoxy)-2,3-dimethyl-8-phenyl- 3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole To a suspension of 0.60 g (1.63 mmol) (6R,7S,8R)-7-hydroxy-6-(2-methoxy-ethoxy)-2,3-dimethyl-8- phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole in dichloro-methane (12 ml) is added 1.25 ml (5.00 mmol) triethylamine, 20.0 mg (0.16 mmol) 4-dimethylaminopyridne and 0.40 g (2.23 mmol) <strong>[60853-81-8]dimethylaminoacetic acid chloride hydrochloride</strong>. The reaction is stirred for further 6 d at 25C. Subsequently the mixture is poured out into water and extracted with dichloromethane three times. The combined organic layers are concentrated in vacuo and purified by column chromatography (dichloromethane / methanol: 100 / 3). The product is reslurried from diethyl ether to give 0.52g (1.15 mmol / 70 %) of the title product as a colourless solid with a melting point of 175C (diethyl ether).

Reference： [1]Patent: WO2005/103057,2005,A1 .Location in patent: Page/Page column 20

22
7-chloro-5,8-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol [ No CAS ]
[ 60853-81-8 ]
7-chloro-5,8-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-yl (dimethylamino)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	Example 15 7-Chloro-5,8-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-yl (dimethylamino)acetate To a solution of 7-chloro-7,8-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol (300 mg), prepared as described above, and dimethylaminoacetyl chloride hydrochloride (564 mg) in dichloromethane (8 mL) was added N-ethyldiiospropylamine (1.4 mL) dropwise at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 16 hours. The solution was diluted with ethyl acetate and washed with water and brine, dried and evaporated. Chromatography (silica gel, hexane-ethyl acetate 5% to 25%) gave 276 mg of 7-chloro-5,8-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-yl (dimethylamino)acetate. 1H-NMR (300 MHz, CDCl3) delta=3.48 (s, 2H), 2.54 (t, J=6.7 Hz, 2H), 2.43 (s, 6H), 2.25-2.15 (m, 5H), 2.00-1.85 (m, 8H), 1.70-1.50 (m, 1H) ppm. 13C-NMR (75 MHz, CDCl3) delta=168.8, 150.0, 138.0, 126.9, 124.8, 123.0, 119.2, 77.1, 59.8, 45.3, 34.1, 28.8, 20.4, 12.9, 12.5 ppm. MS: (m/z)=338 (M+H+).

Reference： [1]Patent: US2006/128790,2006,A1 .Location in patent: Page/Page column 68

Yield	Reaction Conditions	Operation in experiment
		20. (7R,8R,9R)-7-(2-Methoxyethoxy)-2,3-dimethyl-8-(N,N-dimethylaminomethyl-carbonyloxy)-9-phenyl-7,8,9,1 0-tetrahydroimidazo[1,2-h][1,7]naphthyridine The title compound of melting point 114-5 C. (diethyl ether) is obtained analogously to example 8 by reaction of (7R,8R,9R)-8-hydroxy-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine with N,N-dimethylglycine chloride hydrochloride prepared in situ.

Yield	Reaction Conditions	Operation in experiment
		21. (7S,8R,9R)-7-(2-Methoxyethoxy)-2,3-dimethyl-8-(N,N-dimethylaminomethyl-carbonyloxy)-9-phenyl-7,8,9,1 0-tetrahydroimidazo[1,2-h][1,7]naphthyridine The title compound of melting point 206-7 C. (diethyl ether) is obtained analogously to example 8 by reaction of (7S,8R,9R)-8-hydroxy-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine with N,N-dimethylglycine chloride hydrochloride prepared in situ.

25
2-(3-aminophenylimino)-3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)thiazolidine-4-one [ No CAS ]
[ 60853-81-8 ]
N-{3-[3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]phenyl}-2-dimethylaminoacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With triethanolamine; In chloroform; ethyl acetate;	To a solution of 2-(3-aminophenylimino)-3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)thiazolidine-4-one (160 mg, 360 mumol) in chloroform (8 mL) was added <strong>[60853-81-8]N,N-dimethylaminoacetyl chloride hydrochloride</strong> (90 mg, 0.58 mmol) and TEA (150 muL, 1.1 mmol). The reaction solution was heated at reflux for 20 h, cooled, and concentrated in vacuo. The crude material was chromatographed (silica gel, 0-50% EtOAc/Hex) to give the title compound (34 mg, 18%) as a yellow solid. 1H-NMR (CDCl3): delta 9.03 (1H, s), 7.50 (2H, d), 7.37 (2H, t), 7.17-7.26 (5H, m), 7.11 (1H, m), 7.05 (1H, t), 6.88 (1H, d), 6.68 (1H, d), 5.03 (2H), 3.60 (3H, s), 3.00 (2H, s), 2.28 (6H, s); MS(ESI): 530 (MH+).

Reference： [1]Patent: US2003/212111,2003,A1

26
3-[2-amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-yn-1-ol [ No CAS ]
[ 60853-81-8 ]
[ 911397-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; at 20℃; for 0.5h;	A solution of 3-[2-amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-yn-1-ol (see example 1, 177 mg, 0.48 mmol) in anhydrous pyridine (3 mL) was treated with N,N-dimethylamino-acetyl chloride hydrochloride (113 mg, 0.72 mmol) at rt for 30 min. Addition of toluene (10 mL) caused the formation of a sticky pellet. The toluene solution was discarded, and the pellet was partitioned between water and DCM. The DCM layer was concentrated, and purifed by flash chromatography (EtOAc/DCM/Et3N 33:66:1, gradually adding MeOH (0-2%)) to afford the title compound. tR=4.51 min. 1H NMR (CDCl3) delta 8.23 (s, 1H), 7.14 (s, 1H), 5.31 (s, 2H), 5.00 (s, 2H), 4.98 (s, 2H), 3.76 (s, 3H), 3.25 (s, 2H), 2.38 (s, 6H), 2.28 (s, 3H), 2.20 (s, 3H).

Reference： [1]Patent: US2006/223797,2006,A1 .Location in patent: Page/Page column 94

27
[ 54394-09-1 ]
[ 60853-81-8 ]
[ 60853-82-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; methanol; water;	EXAMPLE 2 To a stirred solution of 4-amino-3-(3-methoxycarbonyl-2-thioureido)diphenyl thioether (7.9 g.) in dimethylformamide (50 ml.) there was added during 5 minutes N,N-dimethylglycyl chloride hydrochloride (3.8 g.). The reaction temperature rose to 37 C. during the addition and a white solid began to separate. The reaction mixture was then stirred and heated at 40-45 C. for 75 minutes, cooled and diluted with acetone (150 ml.). The solid was collected on a filter, washed with acetone and sucked dry. This solid was dissolved in a boiling mixture of methanol (100 ml.) and water (10 ml.), and the solution was treated with decolourising charcoal, filtered hot and allowed to crystallise to give 3-(3-methoxycarbonyl-2-thioureido)-4-(2-dimethylaminoacetamido)diphenyl thioether hydrochloride (5.25 g.), in the form of a white crystalline solid, m.p. 192-193 C. (with decomposition).
	In N-methyl-acetamide; methanol; water;	(c) To a stirred solution of 4-amino-3-(3-methoxycarbonyl-2-thioureido)diphenyl thioether (7.9 g) in dimethylformamide (50 ml) there was added during 5 minutes N,N-dimethylglycyl chloride hydrochloride (3.8 g). The reaction temperature rose to 37 C during the addition and a white solid began to separate. The reaction mixture was then stirred and heated at 40-45 C for 75 minutes, cooled and diluted with acetone (150 ml). The solid was filtered off, washed with acetone and sucked dry. This solid was dissolved in a boiling mixture of methanol (100 ml) and water (10 ml), and the solution was treated with decolourising charcoal, filtered hot and allowed to crystallise to give 3-(3-methoxycarbonyl-2-thioureido)-4-(2-dimethylaminoacetamido)diphenyl thioether hydrochloride (5.25 g), in the form of a white crystalline solid, m.p. 192-193 C (with decomposition).

Reference： [1]Patent: US4034107,1977,A
[2]Patent: US4071528,1978,A

28
[ 60854-12-8 ]
[ 60853-81-8 ]
[ 60854-07-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In N-methyl-acetamide; chloroform; water;	EXAMPLE 8 A stirred solution of 2-amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzene (8.35 g.) in dry dimethylformamide (60 ml.) was treated at room temperature with N,N-dimethylglycyl chloride hydrochloride (5.53 g.). The mixture was heated to 40-50 C. for 45 minutes, then cooled, and diluted with diethyl ether (900 ml.). An oil precipitated which crystallized on standing. This solid was filtered off, washed with diethyl ether (100 ml.), and suspended in a mixture of chloroform (100 ml.) and water (100 ml.). Sodium carbonate (3.5 g.) was added and the mixture was stirred for 20 minutes. The chloroform layer was separated and the aqueous layer was extracted twice with chloroform (2* 50 ml.). The organic layers were combined, dried over magnesium sulphate and evaporated to dryness. The residual solid was recrystallized from isopropanol to give 4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)benzene (8.5 g.), m.p. 142 C. (with decomposition). By proceeding in a similar manner but replacing the 2-amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzene used as starting material by the appropriate quantities of 2-amino-4-benzylthio-1-(3-methoxycarbonyl-2thioureido)benzene, 2-amino-4-n-butylthio-1-(3-methoxycarbonyl-2-thioureido)benzene, 2-amino-4-cyclopentylthio-1-(3-methoxycarbonyl-2-thioureido)benzene, and 2-amino-4-(2-ethylthioethylthio)-1-(3-methoxycarbonyl-2-thioureido)benzene, respectively, there were prepared
	With sodium carbonate; In N-methyl-acetamide; chloroform; water;	(e) A stirred solution of 2-amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzene (8.35 g) in dry dimethylformamide (60 ml) was treated at room temperature with N,N-dimethylglycyl chloride hydrochloride (5.53 g). The mixture was heated to 40-50 C for 45 minutes, then cooled, and diluted with diethyl ether (900 ml). An oil precipitated which crystallized on standing. This solid was filtered off, washed with diethyl ether (100 ml), and suspended in a mixture of chloroform (100 ml) and water (100 ml). Sodium carbonate (3.5 g) was added and the mixture was stirred for 20 minutes. The chloroform layer was separated and the aqueous layer was extracted twice with chloroform (2 * 50 ml). The organic layers were combined, dried over magnesium sulphate and evaporated to dryness. The residual solid was recrystallized from isopropanol to give 4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-(2-dimethylaminoacetamido)benzene (8.5 g), m.p. 142 C (with decomposition). By proceeding in a similar manner but replacing the 2-amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzene used as starting material by the appropriate quantities of

Reference： [1]Patent: US4034107,1977,A
[2]Patent: US4071528,1978,A

29
[ 54394-52-4 ]
[ 60853-81-8 ]
4-(3-methoxycarbonyl-2-thioureido)-3-(2-dimethylaminoacetamido)diphenyl sulphoxide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	EXAMPLE 9 A stirred solution of 3-amino-4-(3-methoxycarbonyl-2-thioureido)diphenyl sulphoxide (0.5 g.) in dry dimethylformamide (5 ml.) was treated at room temperature with N,N-dimethylglycyl chloride hydrochloride (0.32 g.). After 90 minutes the solution was poured into diethyl ether (50 ml.). The resulting oil solidified, and the solid was filtered off and recrystallized from a mixture of methanol and diethyl ether to give 4-(3-methoxycarbonyl-2-thioureido)-3-(2-dimethylaminoacetamido)diphenyl sulphoxide hydrochloride (0.1 g.), m.p. 195-197 C. The 3-amino-4-(3-methoxycarbonyl-2-thioureido)diphenyl sulphoxide, used as starting material, was prepared as follows:

Reference： [1]Patent: US4034107,1977,A

30
[ 375798-54-2 ]
[ 60853-81-8 ]
[ 375824-71-8 ]

Yield	Reaction Conditions	Operation in experiment
		Example 10 Synthesis of {(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2-oxo-2,3-dihydro-1H-indol-1-yl }methyl (dimethylamino)acetate Following the procedure of Example 2, the title compound was prepared from 2-chloro-N,N-dimethyl-2-oxoethanaminium chloride and (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one.

Reference： [1]Patent: US2003/176399,2003,A1

31
4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)amide trifluoroacetic acid salt [ No CAS ]
[ 60853-81-8 ]
[ 885692-52-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 4.66667h;	A mixture of 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt (as prepared in Example 14, step (b), 655 mg, 1.30 mmol) in DCM (15 mL) was cooled to 0 C. and DIEA (0.92 mL, 5.2 mmol) was added. Dimethylaminoacetyl chloride hydrochloride (211 mg, 1.3 mol) was then added portion wise over 10 min. The reaction mixture was stirred at 0 C. for 30 min and allowed to warm to RT and stirred for 2 h. Solvent was removed in vacuo and the resulting residue was partitioned between brine and DCM. The organic layer was separated, dried (Na2SO4) and concentrated. The residue obtained was purified on silica (5% MeOH: DCM) to obtain 432 mg (70%) of the title compound as a white solid. 1H-NMR (CDCl3; 400 MHz): delta 9.49 (s, 1H), 8.24 (d, 1H, J=2.3 Hz), 7.70 (s, 1H), 7.12 (dd, 1H, J=8.4, 2.1 Hz), 7.01 (s, 1H), 5.82 (m, 1H), 4.75 (d, 1H, J=13.4 Hz), 4.13 (d, 1H, J=13.4 Hz), 3.57 (d, 1H, J=14.2 Hz), 3.18 (d, 1H, J=14.2 Hz), 3.12 (td, 1H, J=13.3, 2.4 Hz), 2.73 (dddd, 1H, J=11.9, 11.9, 3.8, 3.8 Hz), 2.65 (ddd, 1H, J=13.3, 13.3, 2.4 Hz), 2.40 (s, 6H), 2.18-2.32 (m, 4H), 1.60-1.98 (m, 8H). Mass spectrum (ESI, m/z): Calcd. for C26H32N6O2, 461.3 (M+H), found 461.2.
70%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2.66667h;	A mixture of 4-cyano-lH-imidazole-2-carboxylic acid (2-cyclohex-l-enyl-4- piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt (as prepared in Example 14, step (b), 655 mg, 1.30 mmol) in DCM (15 mL) was cooled to 0 C and DIEA (0.92 mL, 5.2 mmol) was added. Dimethylaminoacetyl chloride hydrochloride (211 mg, 1.3 mol) was then added portion wise over 10 min. The reaction mixture was stirred at 0 C for 30 min and allowed to warm to RT and stirred for 2 h. Solvent was removed in vacuo and the resulting residue was partitioned between brine and DCM. The organic layer was separated, dried (Na2SO4) and concentrated. The residue obtained was purified on silica (5 % MeOH: DCM) to obtain 432 mg (70 %) of the title compound as a white solid. 1H-NMR (CDCl3; 400 MHz): delta 9.49 (s, IH), 8.24 (d, IH, J = 2.3 Hz)3 7.70 (s, IH), 7.12 (dd, IH, J = 8.4, 2.1 Hz), 7.01 (s, IH), 5.82 (m, IH), 4.75 (d, IH, J = 13.4 Hz), 4.13 (d, IH, J = 13.4 Hz), 3.57 (d, IH, J = 14.2 Hz), 3.18 (d, IH, J = 14.2 Hz), 3.12 (td, IH, J = 13.3, 2.4 Hz), 2.73 (dddd, 1 H, J = 1 1.9, 1 1.9, 3.8, 3.8 Hz), 2.65 (ddd, IH, J = 13.3, 13.3, 2.4 Hz), 2.40 (s, 6H), 2.18-2.32 (m, 4H), 1.60-1.98 (m, 8H). Mass spectrum (ESI, m/z): Calcd. for C26H32N6O2, 461.3 (M+H), found 461.2.

Reference： [1]Patent: US2006/281788,2006,A1 .Location in patent: Page/Page column 68
[2]Patent: WO2007/48088,2007,A2 .Location in patent: Page/Page column 104
[3]Journal of Medicinal Chemistry,2011,vol. 54,p. 7860 - 7883

32
[ 60853-81-8 ]
[ 98-18-0 ]
[ 848051-96-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydrogencarbonate; In water; acetone; at 0 - 20℃; for 15.75h;	Intermediate 92 : 2-Dimethylamino-N-\|3-(sulfamogammal)phengammall-acetamidelambda solution of 1 -aminobenzenc-3 -sulfonamide (1.5 g; 8.7 mmol; 1 eq) in a mixutre of acetone (10 mL) and water (10 mL) is stirred at room temperature. Dimethyl aminoacctyl chloride hydrochloride (2.1 g; 13.1 mmol; 1.5 eq) is added at 00C followed by the addition Of NaHCO3 (2.2 g) over 15 min. After 30 min, the reaction mixture stirred at room temperature for 15 h. The reaction is completed by addition of dimethylaminoacetyl chloride hydrochloride (1.9 g; 12.02 mmol: 1.4 eq). The reaction mixture is then filtered and the solid is washed with MeOH and ACN. The filtrate is concentrated to dryness and purified by chromatography using MeOH as elucnt, affording 1.9 g (85%) of the title compound as a yellow solid. 1H NMR (DMSO-cV) delta 10.19 (s, I H), 8.28-8.24 (m, IH), 7.80-7.75 (m, IH), 7.52-7.45 (m, 2H), 7.33 (s, 2H), 3.09 (s, 2H), 2.28 (s, 6H). HPLC (max plot) 68%; Rt 1.56 min. UPLC/MS: (ES+): 258.1, ( ES-): 256.2.
	With sodium hydrogencarbonate; In water; acetone; at 0 - 20℃; for 15.75h;	A flask was charged with 3-aminobenzene sulfonamide (3.3 g5 19 mmol), and 20 mL of 1 : 1 acetone:H2theta. The solution was stirred at room temperature until the aminobenzene sulfonamide had dissolved. The flask was then cooled in an ice bath and dimethylamino-acetyl chloride HCl (4.6 g, 29 mmol) was added. To the resulting slurry sodium bicarbonate (4.8 g, 57 mmol) was added over a 15 m period. After 30 min the reaction was removed from the ice bath and allowed to stir at room temperature for 15 h. The reaction mixture was then filtered and washed with methanol and acetonitrile. The filtrate was dried on a rotary evaporator to yield 2-(dimetyhlamino)-N-(3- sulfamoylphenyl)acetamide5 which was submitted to the next step without further purification. MS (EI) Ci0Hi5N3O3S: 258.0 (MH+).
	With sodium hydrogencarbonate; In water; acetone; at 0 - 20℃; for 15.75h;	Scheme A[00230] A flask was charged with 3-aminobenzene sulfonamide (3.3 g, 19 mmol), and 20 mL of 1:1 acetone .1H2O. The solution was stirred at room temperature until the aminobenzene sulfonamide had dissolved. The flask was then cooled in an ice bath and dimethylamino-acetyl chloride HCl (4.6 g, 29 mmol) was added. To the resulting slurry sodium bicarbonate (4.8 g, 57 mmol) was added over a 15 m period. After 30 min the reaction was removed from the ice bath and allowed to stir at room temperature for 15 h. The reaction mixture was then filtered and washed with methanol and acetonitrile. The filtrate was dried on a rotary evaporator to yield 2-(dimethylamino)-JV-(3-sulfamoyl- phenyl)acetamide, which was submitted to the next step without further purification. MS (EI) m/z C10H15N3O3S: 258.0

Reference： [1]Patent: WO2008/101979,2008,A1 .Location in patent: Page/Page column 91-92
[2]Patent: WO2008/21389,2008,A2 .Location in patent: Page/Page column 301
[3]Patent: WO2007/44729,2007,A2 .Location in patent: Page/Page column 239

33
2,5-dimethyl-2H-pyrazole-3-carboxylic acid (3-{3-[(4-hydroxymethyl-phenylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-6-carbonyl}-phenyl)-amide [ No CAS ]
[ 60853-81-8 ]
dimethylamino-acetic acid 4-[(6-{3-[(2,5-dimethyl-2H-pyrazole-3-carbonyl)-amino]-benzoyl}-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-amino]-benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 2h;	EXAMPLE 332; Dimethylamino-acetic acid 4-[(6-{3-[(2,5-dimethyl-2H-pyrazole-3-carbonyl)-amino]-benzoyl}-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-amino]-benzyl ester; In a dry 50 mL round bottomed flask, 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid (3-{3-[(4-hydroxymethyl-phenylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-6-carbonyl}-phenyl)-amide (as prepared in Example 331, 0.020 mg, 0.039 mmol) was dissolved in DMF (1 mL), under Ar(g). Dimethylaminoacetyl chloride hydrochloride (9.32 mg, 0.059 mmol) was then added followed by triethylamine (0.016 mL, 0.117 mmol). The mixture was stirred at room temperature for 2 hours after which the reaction mixture was partitioned between EtOAc (5 mL) and brine (5 mL). The organic layer was extracted with brine (3×5 mL). The organic layers were combined and then concentrated in vacuo. The crude residue was then chromatographed over silica (EtOAc/MeOH gradiant was used starting from 1% MeOH up to 5% MeOH). The pure product was isolated as a yellow solid (15.5 mg, 0.026 mmol, 67%).

Reference： [1]Patent: US2007/32478,2007,A1 .Location in patent: Page/Page column 147

34
[ 60853-81-8 ]
[ 68-26-8 ]
[ 1040750-85-3 ]

Yield	Reaction Conditions	Operation in experiment
75.5%	With triethylamine; In acetonitrile; at 20℃; for 5h;	28.6 g (0.1 mol) of retinol was dissolved in 300 ml of acetonitril. 25 ml of tri- ethylamine was added into the reaction mixture. 16 g of <strong>[60853-81-8]N,N-dimethylaminoacetyl chloride hydrochloride</strong> was added into the reaction mixture. The mixture was stirred for 5 h at RT. The solid was removed by filtration. The solution was evaporated to dryness. 500 ml of ethyl acetate was added into the residue. 200 ml of 5% of sodium c arbonate solution was added into the mixture with stirring. The organic solution is collected and washed with water (After drying, it yielded 31 g of the desired product (75.5%). Hygroscopic product; Elementary analysis: C H ClNO ; MW: 408.02. Calculated % C: 70.65; H: 9.39; Cl: 8.69; N: 3.43; O: 7.84; Found % Q70.60; H: 9.46; Cl: 8.71; N: 3.42; O: 7.81.
75.5%	With triethylamine; In acetonitrile; at 20℃; for 5h;	28.6 g (0.1 mol) of retinol were dissolved in 300 ml of acetonitrile.To this reaction mixture 25 ml of triethylamine was added. To this reaction mixture was added 16 g of N, N-dimethylaminoacetyl chloride hydrochloride. The mixture was stirred at room temperature for 5 hours. Solids were removed by filtration. The solution was evaporated to dryness. To this residue 500 ml of ethyl acetate was added. To this mixture was added 200 ml of 5% sodium carbonate solution with stirring. The organic solution was collected and washed with water (after drying 31 g of the desired product was obtained (75.5%))
75.5%	With triethylamine; In acetonitrile; at 20℃; for 5h;	28.6 g (0.1 mol)Of retinol were dissolved in 300 ml of acetonitrile.To this reaction mixture 25 ml of triethylamine was added.To this reaction mixture 16 gOf N, N-dimethylaminoacetyl chloride hydrochloride were added.The mixture was stirred at room temperature for 5 hours.Solids were removed by filtration.The solution was evaporated to dryness.500 ml of ethyl acetate was added to the residue.To this mixture was added 200 ml of 5% sodium carbonate solution with stirring.The organic solution was collected and washed with water (after drying 31 g of the desired product was obtained (75.5%).

75.5%

With triethylamine; In acetonitrile; at 20℃; for 5h;

28.6 g (0.1 mol) of retinol were dissolved in 300 ml of acetonitrile.To this reaction mixture 25 ml of triethylamine was added.To this reaction mixture was added 16 g ofN, N-dimethylaminoacetyl chloride hydrochloride was added.The mixture was stirred at room temperature for 5 hours.Solids were removed by filtration. The solution was evaporated to dryness.500 ml of ethyl acetate was added to the residue.To this mixture was added 200 ml of 5% sodium carbonate solution with stirring.The organic solution was collected and washed with water (after drying,31 g of the desired product were obtained (75.5%).

Reference： [1]Patent: WO2008/87493,2008,A1 .Location in patent: Page/Page column 21
[2]Patent: JP2015/221830,2015,A .Location in patent: Paragraph 0058
[3]Patent: JP2017/160260,2017,A .Location in patent: Paragraph 0058
[4]Patent: JP2017/160261,2017,A .Location in patent: Paragraph 0058

35
[ 60853-81-8 ]
[ 53269-34-4 ]
[ 1059131-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 1.5h;	Example 4; 7V^V-Dimethyl-2-[l-(phenylsulfonyl)-l,5-dihydropyrrolo[4,3,2-de]isoquinolin- 4(3H)-yl] ethanamine bis(trifluoroacetate)1, 3,4, 5-tetrahydropyrrolo[4,3,2-de]isoquino line, Intermediate 3 (45 mg, 0.28 mmol), NEt3 (236 muL, 1.71 mmol) and JV,JV-dimethylgrycyl chloride hydrochloride (90 mg, 0.57 mmol) were dissolved in dry DCM (10 mL) by sonication and stirred at room temperature for 1.5 h. The mixture was extracted with DCM (x2) and aq. sat. Na2Ctheta3/brine. The organic layers were combined dried (Na2SO4), filtered and concentrated to give 69 mg crude material.

Reference： [1]Patent: WO2008/110598,2008,A1 .Location in patent: Page/Page column 32

36
[ 60853-81-8 ]
[ 4029-44-1 ]
N-(4-[(3-chloroquinoxalin-2-yl)amino]sulfamoyl}phenyl)-2-dimethylamino-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	Intermediate 137 : ^; To a suspension of 4-anuno-N-(3-chloroquinoxalin-2-yl)benzcncsulfonaraide (2 g; 4.5 nimol; 1 eq) in DCM (100 mL) is added dimcthylaminoacetyl chloride hydrochloride (710 mg; 4.5 mmol; 1 eq) and N-ethyldiisopropylamine (2.3 mL; 13.5 mmol: 3 eq) and the reaction mixture is stirred at room temperature overnight. To complete the reaction, dimethylaminoacetyl chloride hydrochloride (1.06 g: 6.74 mmol; 1.5 cq) is added and the reaction mixture is allowed to stir another 2 days. The precipitate formed is filtered off and the filtrate is treated with a solution of citric acid. The precipitate in the organic phase is filtered and the aqueous phase is basificd with Na2CO3. The product is extracted with DCM and the organic phase is concentrated to near dryness to afford 1.5 g (80%) of the title compound as a yellow powder. HPLC (max piot) 85%; Rt 2.37 mm. UPLC/MS (ES+) 420.2, (ES-) 418.3.

Reference： [1]Patent: WO2008/101979,2008,A1 .Location in patent: Page/Page column 107

37
[ 1080007-07-3 ]
[ 60853-81-8 ]
[ 1080007-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; N,N-dimethyl-formamide; for 88h;	Example 3Methyl 2-(4-((N-(3-(4-amino-2-butyl-lH-imidazo[4,5-c]quinolin-l-yl)propyl)-2-(dimethylamino)acetamido)methyl)phenyl)acetate; The product from example 1 (15mg) was dissolved in a mixture of DMF:DCM, 1:1 (5 mL) and 7V,7V-dimethylglycyl chloride hydrochloride salt (8mg) and Et3N (0.0 ImL) were added. The reaction mixture was stirred for 72h. More 7V,7V-dimethylglycyl chloride hydrochloride salt (0.05Og) and Et3N (0.06mL) were added, the mixture was stirred for a further 16h. The product was purified via RPHPLC.1H NMR delta (CD3OD) 8.05 - 7.96 (IH, m), 7.73 - 7.66 (IH, m), 7.54 - 7.45 (IH, m), 7.38 - 7.29 (IH, m), 7.17 - 7.01 (4H, m), 4.63 - 4.45 (4H, m), 3.63 (3H, s), 3.56 (2H, s), 3.51 - 3.33 (2H, m), 3.01 (IH, s), 2.94 - 2.85 (2H, m), 2.28 (3H, s), 2.22 - 2.13 (IH, m), 2.04 (4H, s), 1.88 - 1.78 (2H, m), 1.52 - 1.42 (2H, m), 1.35 - 1.25 (IH, m), 1.00 (3H, s) <n="53"/>MS: APCI (+ve): 545

Reference： [1]Patent: WO2008/135791,2008,A1 .Location in patent: Page/Page column 51

38
[ 1093306-62-7 ]
[ 60853-81-8 ]
C₂₅H₂₉N₇O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 20℃;	Example 64A (81 mg, 0.207 mmol) was dissolved in methylene chloride (2 mL) and pyridine (0.5 mL). Dimethylaminoacetylchloride hydrochloride, 80% (120 mg, 0.607 mmol) <n="82"/>was added in three portions over 2 hours and the mixture was stirred at ambient temperature overnight. Trifluoroacetic acid (2 mL) was added and the mixture was stirred for 3 hours. The mixture was diluted with methylene chloride and washed with 1 N sodium hydroxide. The organic layer was absorbed on silica gel and purified using silica gel chromatography eluting with a gradient of 5-15% methanol in dichloromethane to afford the title compound. 1H NMR (300 MHz, DMSO-d*) delta ppm 12.77 (s, 1 H) 10.05 (s, 1 H) 8.58 (s, 1 H) 8.24 (s, 1 H) 7.82 (d, J=8.65, 1.53 Hz, 1 H) 7.50 (d, J=8.82 Hz, 1 H) 7.30 - 7.44 (m, 5 H) 5.64 (s, 2 H) 3.16 - 3.20 (m, 2 H) 2.34 (s, 6 H). MS (ESI+) m/z 376.1 (M+H)+.

Reference： [1]Patent: WO2008/154241,2008,A1 .Location in patent: Page/Page column 80-81

39
[ 1093307-38-0 ]
[ 60853-81-8 ]
[ 1093307-39-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 20℃; for 2h;	To a mixture of Example 282B (24.43 g, 78 mmol), potassium carbonate (81 g, 587 mmol) and <strong>[60853-81-8]2-<strong>[60853-81-8](dimethylamino)acetyl chloride hydrochloride</strong></strong> (43.3 g, 274 mmol) was added tetrahydrofuran (200 mL). The reaction mixture was stirred at room temperature for about 2 hours. The reaction mixture was filtered and the filtrate was washed with water (50 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3 x 100 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with methanol in dichloromethane (5%) to afford the title compound. 1H NMR (400 MHz, DMSO-d^) delta ppm 10.72 (s, IH), 8.19 (d, IH, J = 1.6), 8.03 (d, IH, J = 9.0), 7.76 (dd, IH, J = 2.0, 9.0), 3.22 (s, 2H), 2.32 (s, 6H), 1.63 (s, 9H).

Reference： [1]Patent: WO2008/154241,2008,A1 .Location in patent: Page/Page column 167

40
C₂₄H₂₉N₃O*2ClH [ No CAS ]
[ 60853-81-8 ]
[ 586411-70-3 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 2887 - 2890

41
[ 1124197-88-1 ]
[ 60853-81-8 ]
[ 1124198-25-9 ]

Yield	Reaction Conditions	Operation in experiment
78%		A solution of ((S)-3-Amino-piperidin-1-yl)-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-methanone, hydrochloride (Example 26, 79 mg, 0.20 mmol) in THF (3 mL) was treated with dimethylaminoacetyl chloride hydrochloride (40 mg, 0.24 mmol) followed by triethylamine (62 muL, 0.44 mmol). The resulting mixture was stirred for 16 hr, evaporated to an oil, and dissolved in water (3 mL). The solution was then basified with a saturated aqueous K2CO3 solution and the precipitated product filtered, washed with water, and air dried to afford product as a colorless solid (69 mg, 78%). 1H NMR (CDCl3) 1.62-1.72 (m, 2H), 1.78-1.84 (m, 1H), 1.94-2.04 (m, 1H), 2.25 (s, 6H), 2.32 (d, J=1.3, 3H), 2.49 (s, 2H), 3.24-3.40 (m, 2H), 3.94-4.04 (m, 2H), 4.12 (br d, J=13.2, 1H), 7.23 (br d, J=7.5, 1H), 7.44 (d, J=4.0, 1H), 7.47 (br s, 1H). 13C NMR 7.9, 23.5, 30.4, 45.6, 46.2, ~51 (br), 63.2, 114.8, 118.8 (q, J=271), 128.3, 129.5, 131.6, 140.2, 155.1 (q, J=40), 157.9, 163.1, 170.7. 19F NMR -63.1. LC/MS 4.59 min, [M+1]+ 445.

Reference： [1]Patent: US2009/62252,2009,A1 .Location in patent: Page/Page column 58

42
[ 312300-45-1 ]
[ 60853-81-8 ]
[ 1116229-47-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine;dmap; In tetrahydrofuran; 1,2-dichloro-ethane; at 65℃;	Step C/lntermediate B77: 1 ,1-dimethylethyl [5-[(lambda/,lambda/-dimethylglycyl)amino]-2- (methyloxy)phenyl]carbamate; To a solution of 1 ,1-dimethylethyl [5-amino-2-(methyloxy)phenyl]carbamate (0.5 g, 2.1 mmol) in 1 :1 THF/DCE (100 ml.) was added triethylamine (1.28 g, 12.6 mmol, Aldrich), 2-dimethylaminoacetyl chloride hydrochloride (0.66g, 4.20 mmol, Alfa Aesar), and catalytic DMAP. After overnight heating at 650C, the crude reaction mixture was washed with brine (50 ml_), evaporated, and purified by column chromatography (dichloromethane to 5% methanol/dichloromethane) to provide 1 ,1- dimethylethyl [5-[(lambda/,lambda/-dimethylglycyl)amino]-2-(methyloxy)phenyl]carbamate (0.44 g, 65%) as a brown solid. ESIMS (M+H)+ = 324.

Reference： [1]Patent: WO2009/20990,2009,A1 .Location in patent: Page/Page column 118

43
[ 635-22-3 ]
[ 60853-81-8 ]
[ 902643-34-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With triethylamine;dmap; In tetrahydrofuran; 1,2-dichloro-ethane; at 65℃;	Intermediate B82: lambda/1-(3-amino-4-chlorophenyl)-lambda/2,lambda/2-dimethylglycinamide; Step A/Intermediate B83: lambda/1-(4-chloro-3-nitrophenyl)-lambda/2,lambda/2-dimethylglycinamide; To a solution of 4-chloro-3-nitroaniline (1.0 g, 5.81 mmol) in 1 :1 THF/DCE (200 ml.) was added triethylamine (3.53 g, 34.9 mmol, Aldrich), 2-dimethylaminoacetyl chloride hydrochloride (1.82 g, 11.6 mmol, Alfa Aesar), and catalytic DMAP (Aldrich). After heating overnight at 650C, the crude reaction mixture was diluted with dichloromethane (300 ml_), washed with saturated NaHCOs (50 ml_), evaporated, and purified by column chromatography (dichloromethane to 5% methanol/dichloromethane) to provide lambda/1-(4-chloro-3-nitrophenyl)-lambda/2,lambda/2- dimethylglycinamide (1.0 g, 67%) as a brown solid. ESIMS (M+H)+ = 258.

Reference： [1]Patent: WO2009/20990,2009,A1 .Location in patent: Page/Page column 121

44
[ 364-76-1 ]
[ 60853-81-8 ]
[ 1116229-56-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With pyridine;dmap; In tetrahydrofuran; 1,2-dichloro-ethane; at 65℃; for 1.5h;	Intermediate B80: lambda/1-(3-amino-4-fluorophenyl)-lambda/2,lambda/2-dimethylglycinamide; Step A/Intermediate B81 : lambda/1-(4-fluoro-3-nitrophenyl)-lambda/2,lambda/2-dimethylglycinamide; To a solution of 4-fluoro-3-nitroaniline (2.48 g, 15.9 mmol) in 1 :1 THF/DCE (200 ml.) was added pyridine (7.54 g, 95.4 mmol, Aldrich), 2-dimethylaminoacetyl chloride hydrochloride (0.66g, 4.20 mmol, Lancaster), and catalytic DMAP (~ 0.10Og). After heating at 650C for 1.5 hrs, the crude reaction mixture was diluted with dichloromethane (300 ml_), washed with saturated NaHCOs (50 ml_), evaporated, and purified by column chromatography (dichloromethane to 5% methanol/dichloromethane) to provide lambda/1-(4-fluoro-3-nitrophenyl)-lambda/2,lambda/2- dimethylglycinamide (3.0 g, 78%) as a brown solid. ESIMS (M+H)+ = 242.

Reference： [1]Patent: WO2009/20990,2009,A1 .Location in patent: Page/Page column 120

45
[ 2267-21-2 ]
[ 60853-81-8 ]
[ 1116229-51-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	With dmap; triethylamine; In dichloromethane; at 20℃; for 24h;	Intermediate 78: lambda^-IS-amino^^trifluoromethoxyJphenylJ-lambda/2,^2- dimethylglycinamide; Step A/Intermediate 79: lambda/1-[3-amino-4-(trifluoromethoxy)phenyl]-lambda/2,lambda/2- dimethylglycinamide; To a solution of 2-trifluoromethoxy-4-amino nitro benzene (5.0Og, 22.5 mmol) in dichloromethane (200 ml.) was added triethylamine (12.2 ml_, 90 mmol, 4.0 equiv.), dimethylaminopyridine (ca 500 mg) and dimethylaminoacetyl chloride hydrochloride (5.3g, 33.8 mmol, 1.50 equiv.). The resulting clear solution was stirred 24 hours and was poured into saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (0 to 10% methonal/CH2CL2) to give lambda/1-[3-amino-4- (trifluoromethoxy)phenyl]-lambda/2,lambda/2-dimethylglycinamide (4.54g, 14.8 mmol, 66% yield) as a brown oil. 1 H NMR (400 MHz, DMSOd6) delta ppm 2.26 (s, 6 H), 3.1 1 (s, 2 H), 7.67 (dd, J=8.97, 1.28 Hz, 1 H), 8.08 (dd, J=9.06, 2.65 Hz, 1 H), 8.60 (d, J=2.74 Hz, 1 H), 10.40 (s, 1 H).

Reference： [1]Patent: WO2009/20990,2009,A1 .Location in patent: Page/Page column 119

46
[ 1149338-44-2 ]
[ 60853-81-8 ]
[ 1149338-49-7 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 1471 - 1476

47
[ 60853-81-8 ]
[ 538366-91-5 ]
[ 1149338-51-1 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 1471 - 1476

48
[ 60853-81-8 ]
[ 538366-87-9 ]
[ 1149338-50-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 1471 - 1476

49
[ 60853-81-8 ]
[ 538366-89-1 ]
[ 1149338-52-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 1471 - 1476

50
[ 1142947-95-2 ]
[ 60853-81-8 ]
[ 1142947-09-8 ]

Yield	Reaction Conditions	Operation in experiment
36%	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 0.5h;	To a solution of 86 (60 mg, 0.135 mmol) in 2 niL of anhydrous DMF was added one drop of Et3N, followed by solid dimethylaminoacetyl chloride hydrochloride salt (32 mg, 0.20 mmol). The reaction mixture was stirred at ambient temperature for 30 min, then filtered through 0.2 u syringe filter and purified by reverse-phase preparative HPLC in CH3CN/H2O system containing 0.1% of TFA. Fractions, containing the product, were combined and poured into EtOAc (30 mL). The solution was treated with saturated aqueous NaHCO3 (2 x 10 mL), washed with brine (2 x 10 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (26 mg, 36% yield).[0409] 1H NMR (500 MHz, DMSO-J6, 80 0C): delta 2.26 (s, 6H), 2.27 (s, 3H), 2.50-2.52 (m, 4H), 2.94 (br s, 2H), 2.99 (br s , 4H), 3.20 (s, 2H), 3.88 (t, J = 5.6 Hz, 2H), 4.68 (s, 2H), 6.49 (dd, J = 8.0, 2.1 Hz, IH), 6.79 (dd, J= 3.6, 1.6 Hz, IH), 7.10 (t, J = 8.1 Hz, IH), 7.22-7.25 (m, 2H), 7.63 (t, J= 2.0 Hz, IH), 7.81 (s, IH), 8.55 (s, IH), 11.30 (s, IH)MS (ES+): m/z 531 (M+H)+

Reference： [1]Patent: WO2009/49028,2009,A1 .Location in patent: Page/Page column 172

51
[ 890019-89-3 ]
[ 60853-81-8 ]
N-((5-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)(phenyl)methyl)-2-(dimethylamino)acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5766 - 5779

52
5-(phenylsulfonyl)-N-piperidin-4-yl-2-(trifluoromethyl)benzenesulfonamide hydrochloride [ No CAS ]
[ 60853-81-8 ]
[ 1095322-79-4 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 105 - 116

53
[ 94643-16-0 ]
[ 60853-81-8 ]
[ 1085226-08-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 969 - 972

54
[ 1085240-76-1 ]
[ 60853-81-8 ]
[ 1085246-38-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 969 - 972

55
[ 94643-16-0 ]
[ 60853-81-8 ]
[ 1085226-08-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 969 - 972

56
[ 1173207-52-7 ]
[ 60853-81-8 ]
[ 1173207-53-8 ]

Yield	Reaction Conditions	Operation in experiment
62%		Example 249Preparation of N-[4-([4-(3-ethyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl)phenyl]carbamoyl}amino)phenyl]-N2,N2-dimethylglycinamide. To the 1-(4-aminophenyl)-3-(4-(3-ethyl-7-morpholino-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl)phenyl)urea (95 mg, 0.207 mmol) and CHCl3 (1.3 mL) was added Et3N (87 muL, 0.622 mmol) stirred for 15 min. and added 2-(dimethylamino)acetyl chloride. HCl (49 mg, 0.311 mmol) followed by DMAP (5 mg). The mixture was stirred overnight and purified by silica gel chromatography using CH2Cl2, MeOH, 7N NH3 in MeOH (10:1:0.22) method to give N-[4-([4-(3-ethyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl)phenyl]carbamoyl}amino)phenyl]-N2,N2-dimethylglycinamide (70 mg, 62% yield) as a beige solid, MS (ESI) m/z=574.4.

Reference： [1]Patent: US2009/181963,2009,A1 .Location in patent: Page/Page column 60

57
[ 1126420-71-0 ]
[ 60853-81-8 ]
[ 1199813-66-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine; In tetrahydrofuran; at 20℃; for 72h;	A solution of 27B (40 mg, 0.089 mmol). dimethyl aminoacetyl chloride hydrochloride (147 mg, 0.93 mmol) and triethylamine (0.26 ml 1.87 mmol) In THF (5 ml) in a 25 ml round- bottomed flask was stirred at room temperature for 72 hours. After evaporating off the solvents, water (3 mL) was added to the flask before filtration. The cake was washed with MeOH (2x ImL), dried by air and then on house vacuum to provide 27C as a yellow solid (36 mg, 75%). This crude product is pure enough for the next reaction without further purification. To the stirring mixture of 27C (36 mg, 0.067 mmol) in THF (5 ml) in a 25 ml round- bottomed flask was added with a solution of lithium hydroxide (0.34 ml of 1 M, 0.34 mmol). The resulting solution was stirred at room temperature for 2 hours. Before concentration under <n="103"/>vacuum, the reaction mixture was neutralized with 1.0 M HCl aqueous solution (0.34 ml, 0.34 mmol). Water (3 ml) was added to the flask before filtration. The cake was washed with MeOH (2x ImL), dried by air and then on house vacuum to provide title compound 116 as a yellow solid (34 mg, 92%). MS found 554.3 for C30H24FN5O5 + H+.

Reference： [1]Patent: WO2009/152200,2009,A1 .Location in patent: Page/Page column 100

58
[ 1226807-61-9 ]
[ 60853-81-8 ]
[ 1226807-69-7 ]

Yield	Reaction Conditions	Operation in experiment
26%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃;	A mixture of 8-chloro-1-(1'H,3H-spiro[2-benzofuran-1,4]-piperidin)-1'-yl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine (0.30 g, 0.74 mmol), N-ethyldiisopropylamine (0.51 ml, 2.94 mmol) and dimethylaminoacetyl chloride hydrochloride (0.21 g, 1.10 mmol) in 12 ml THF were stirred at room temperature over night. Extraction with ethyl acetate and chromatography (20 g Flasch-NH2 Isolute column, ethyl acetate) yielded 93 mg (26%) 2-[8-chloro-1-(1'H,3H-spiro[2-benzofuran-1,4'-piperidin]-1'-yl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-5(6H)-yl]-N,N-dimethyl-2-oxoethanamine as white solid. MS m/e: 493 (M+H+).

Reference： [1]Patent: US2010/120751,2010,A1 .Location in patent: Page/Page column 28

59
[ 1292230-84-2 ]
[ 60853-81-8 ]
[ 1226884-54-3 ]

Yield	Reaction Conditions	Operation in experiment
20.39%	With triethylamine; In methanol; dichloromethane; at 20℃; for 1h;	2-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-

Reference： [1]Patent: WO2010/53438,2010,A1 .Location in patent: Page/Page column 72; 73

60
[ 1234344-53-6 ]
[ 60853-81-8 ]
[ 1234344-55-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3974 - 3984

61
[ 1234344-54-7 ]
[ 60853-81-8 ]
[ 1234344-56-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3974 - 3984

62
[ 1234344-59-2 ]
[ 60853-81-8 ]
[ 1234344-61-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3974 - 3984

63
[ 1234344-60-5 ]
[ 60853-81-8 ]
[ 1234344-62-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3974 - 3984

64
[ 1227243-07-3 ]
[ 60853-81-8 ]
[ 1227243-16-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 40℃; for 72h;	Example 21. D-21D-12 D-21[00152] Synthesis of N-{5-[8-(3-Chloro-phenyl)-2-methyl-imidazo[l,2-a]pyridin-6- ylmethyl]-pyridin-2-yl}-2-dimethylamino-acetamide (D-21): To a mixture of compound D-12 (20 mg, 0.057 mmol) and dimethylamino acetyl chloride hydrochloride (23 mg, 0.14 mmole) in DCM (2 ml), was added diisopropylethylamine (37 mg, 0.3 mmole). The reaction mixture was stirred at 40 oC for 3 days and diluted with DCM (5 ml) and sat. NaHCO3 aq. The aqueous portion was extracted with DCM (3 x 10 ml), the organic portions were combined, washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by column chromatography utilizing MeOH/DCM as the eluent to give 13 mg of D- 21 in 53 % yield. To a solution of D-21 (13 mg) in DCM (3 ml), was added HCl in Et20 (2N, 0.1 ml), solid was washed with ether to give 13 mg of D-21 HCl salt as solid. 1H-NMR (400 MHz, DMSO-d6): 2.47 (3H, s), 2.85 (3H, s), 2.87 (3H, s), 4.14 (2H, s), 4.18 (2H, br), 7.65 (3H, m), 7.78 (IH, br), 7.84 (IH, dd, J= 8 and 2.4 Hz), 7.90 (IH, br), 8.00 (IH, br), 8.16 (IH, br), 8.40 (IH, d, J=2.4 Hz), 8.82 (IH, br, 10.0 (IH, br), 11.15 (IH, s), 14.0 (IH, br). MS(APCI+): 434.1 (M+l). LC-MS: 99 %.

Reference： [1]Patent: WO2010/59836,2010,A1 .Location in patent: Page/Page column 56

65
5-[8-(3-chloro-phenyl)-2-methyl-imidazo[1,2-a]pyridin-6-ylmethyl]-pyridin-2-ylamine hydrochloride [ No CAS ]
[ 60853-81-8 ]
[ 1227243-16-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 40℃; for 72h;	To a mixture of compound D-12 (20 mg, 0.057 mmol) and dimethylaminoacetyl chloride hydrochloride (23 mg, 0.14 mmole) in DCM (2 ml), was added diisopropylethylamine (37 mg, 0.3 mmole). The reaction mixture was stirred at 40 0C for 3 days and diluted with DCM (5 ml) and sat. NaHCtheta3 aq. The aqueous portion was extracted with DCM (3 x 10 ml), the organic portions were combined, washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by column chromatography utilizing MeOH/DCM as the eluent to give 13 mg of D- 21 in 53 % yield. To a solution of D-21 (13 mg) in DCM (3 ml), was added HCl in Et2O (2N, 0.1 ml), solid was washed with ether to give 13 mg of D-21 HCl salt as solid. 1H-NMR (400 MHz, DMSO-d6): 2.47 (3H, s), 2.85 (3H, s), 2.87 (3H, s), 4.14 (2H, s), 4.18 (2H, br), 7.65 (3H, m), 7.78 (IH, br), 7.84 (IH, dd, J= 8 and 2.4 Hz), 7.90 (IH, br), 8.00 (IH, br), 8.16 (IH, br), 8.40 (IH, d, J=2.4 Hz), 8.82 (IH, br, 10.0 (IH, br), 11.15 (IH, s), 14.0 (IH, br). MS(APCI+): 434.1 (M+l). LC-MS: 99 %.

Reference： [1]Patent: WO2010/59838,2010,A2 .Location in patent: Page/Page column 115

66
[ 879609-23-1 ]
[ 60853-81-8 ]
[ 76-05-1 ]
2-(dimethylamino)-N-(4-(2-acetamidobenzo[d]thiazol-4-yloxy)-6-(4-(trifluoromethyl)phenyl)pyrimidin-2-yl)acetamide trifluoroacetic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(c) 2-(Dimethylamino)-N-(4-(2-acetamidobenzo[d]thiazol-4-yloxy)-6-(4-(trifluoromethyl)phenyl)pyrimidin-2-yl)acetamide, trifluoroacetic acid salt. To a solution of N-(4-(2-amino-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide from step (b) above (89 mg, 0.2 mmol) in dioxane (4 mL) was added NaH (60% in mineral oil, 40 mg, 1 mmol, Aldrich) and the mixture was stirred at room temperature for 5 min. Dimethylaminoacetyl chloride HCl salt (79 mg, 0.5 mmol, Lancaster) was added, and the reaction mixture was stirred for 30 min at room temperature. The mixture was diluted with water (15 mL) and extracted with EtOAc (40 mL). The organic phase was washed with brine (10 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue purified by silica gel column chromatography (10% MeOH/DCM) to give the crude product. Additional purification of the product by preparative HPLC [gradient 20-80% MeCN (0.1% TFA)/H2O (0.1% TFA)] gave the title compound as a TFA salt. MS (ESI, pos. ion) m/z: 531 (M+1).

Reference： [1]Patent: US2006/58308,2006,A1 .Location in patent: Page/Page column 59

67
[ 1253799-32-4 ]
[ 60853-81-8 ]
[ 1253799-39-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	In DMPU(l,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone); acetonitrile; for 4.5h;Inert atmosphere;	To a solution of compound 69 (10.0 mg, 0.020 mmol, 1 equiv) inDMPU:CH3CN (3:1, 400 muL) was added <strong>[60853-81-8]2-<strong>[60853-81-8](dimethylamino)acetyl chloride hydrochloride</strong></strong> (5.6 mg, 0.030 mmol, 1.5 equiv). The solution lightens to yellow. After 1.5h, another 1.5 equiv of the acetyl chloride was added. After 3 h, the solvent was removed under reduced pressure. Removal of excess DMPU was achieved by precipitation of the desired salt via addition of HCl in MeOH (0.5 M, 200 muL) followed by Et2O (3.5 mL). The precipitate was filtered off on Celite with Et2O wash, then rinsed off with MeOH and concentrated under reduced pressure. Preparative reverse phase HPLC of the resulting oil afforded 5.58 mg of the desired compound 73 (45%): 1H NMR (400 MHz, CD3OD) delta 8.25 (d, J= 1 1.0 Hz, 1 H), 4.23 (s, 2 H), 4.10 (s, 1 H), 3.09-2.94 (m, 14 H), 2.56 (d, 15.9 Hz, 1 H), 2.04-1.98 (m, 1 H), 1.95- 1.85 (m, 1 H), 1.26 (s, 3 H); MS (ESI) m/z 547.16 (M+H).

Reference： [1]Patent: WO2010/126607,2010,A2 .Location in patent: Page/Page column 176/251

68
3-[4-(piperazin-1-yl)phenyl]-6-(pyrid-3-yl)-9H-pyrrolo[2,3-b:5,4-c']dipyridine hydrochloride [ No CAS ]
[ 60853-81-8 ]
[ 1201789-97-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With pyridine; N-ethyl-N,N-diisopropylamine; for 1.5h;Inert atmosphere; Keller tube;	Compound 120 is prepared as for 119 using compound 115 (70 mg, 0.136 mmol) to give a bright white solid (42 mg, 63%).MS: m/z=492 (ES+).1H NMR (300 MHz, DMSO-d6) delta ppm 12.30 (s, 1H), 9.37 (s, 1H), 9.03 (s, 2H), 8.99 (s, 1H), 8.90 (s, 1H), 8.60 (d, 1H), 8.51 (dd, 1H), 7.72 (d, 2H), 7.55 (dd, 1H), 7.15 (d, 2H), 3.71 (t, 2H), 3.64 (t, 2H), 3.25 (m, 4H), 3.22 (s, 2H), 2.25 (s, 6H).

Reference： [1]Patent: US2011/178053,2011,A1 .Location in patent: Page/Page column 90

69
3-[3-(piperazin-1-yl)phenyl]-6-(pyrid-3-yl)-9H-pyrrolo[2,3-b:5,4-c']dipyridine hydrochloride [ No CAS ]
[ 60853-81-8 ]
[ 1201789-96-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With pyridine; N-ethyl-N,N-diisopropylamine; for 1.5h;Keller tube; Inert atmosphere;	Compound 117 (70 mg, 0.136 mmol) and N,N-dimethylglycyl chloride hydrochloride (49 mg, 0.310 mmol) are placed in a Keller tube. Anhydrous pyridine (1 ml) is added under nitrogen, followed by N,N-diisopropylethylamine (148 mg, 1.15 mmol). The orange suspension is then stirred for 1.5 hours, and then diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane containing 10% tetrahydrofuran (5×30 ml). The combined organic phases are dried over MgSO4 and concentrated to dryness. The solid obtained is dried under reduced pressure at 50 C. to give compound 119 in the form of a cream-white solid (56 mg, 84%).MS: m/z=492 (ES+).1H NMR (300 MHz, DMSO-d6) delta ppm 12.37 (s, 1H), 9.38 (s, 1H), 9.06 (s, 1H), 9.05 (s, 1H), 8.99 (s, 1H), 8.96 (s, 1H), 8.60 (t, 1H), 8.52 (dt, 1H), 7.55 (dd, 1H), 7.41 (t, 1H), 7.38 (s, 1H), 7.27 (d, 1H), 7.03 (d, 1H), 3.68 (m, 4H), 3.52 (s, 2H), 3.32 (m, 4H), 2.41 (s, 61-1).

Reference： [1]Patent: US2011/178053,2011,A1 .Location in patent: Page/Page column 89

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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 60853-81-8 ]

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[ 60853-81-8 ] Synthesis Path-Upstream 1~2

[ 60853-81-8 ] Synthesis Path-Downstream 1~69

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