[ CAS No. 144550-76-5 ] {[proInfo.proName]}

Name: 144550-76-5|Methyl 2-amino-4-iodobenzoate|97%
Brand: Ambeed
SKU: A128451
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Quality Control of [ 144550-76-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 144550-76-5 ]

SDS Specification

Alternatived Products of [ 144550-76-5 ]

Product Details of [ 144550-76-5 ]

CAS No. :	144550-76-5	MDL No. :	MFCD13182440
Formula :	C₈H₈INO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FSNRVHNXSYBHSI-UHFFFAOYSA-N
M.W :	277.06	Pubchem ID :	18929930
Synonyms :

Calculated chemistry of [ 144550-76-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.84
TPSA :	52.32 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) :	-6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.02
Log Po/w (XLOGP3) :	2.53
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	2.21
Log Po/w (SILICOS-IT) :	1.94
Consensus Log Po/w :	2.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.39
Solubility :	0.113 mg/ml ; 0.000408 mol/l
Class :	Soluble
Log S (Ali) :	-3.28
Solubility :	0.147 mg/ml ; 0.000531 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.06
Solubility :	0.24 mg/ml ; 0.000865 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.81

Safety of [ 144550-76-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 144550-76-5 ]

* 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 [ 144550-76-5 ]
Downstream synthetic route of [ 144550-76-5 ]

[ 144550-76-5 ] Synthesis Path-Upstream 1~6

1
[ 67-56-1 ]
[ 117324-10-4 ]
[ 144550-76-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	at 0 - 65℃; for 52 h;	To 2-acetylamino-4-iodo-benzoic acid (13.8 g, 45.3 mmol) in 200 mL of dry methanol was added SOCl₂ (32.7 mL, 453 mmol) dropwise at 0 °C. The reaction mixture was then heated at 65 °C for 2 h. The reaction was then cooled to 0 °C, an additional portion of SOCl₂ (10 mL, 137 mmol) was added, and the reaction was heated at 65 ⁰C for 2 h. The reaction was then cooled to 0 °C, a final portion of SOCl₂ (10 mL, 137 mmol) was added, and the reaction was heated at 65 °C for 48 h. The reaction was then cooled to 22 °C and concentrated in vacuo The resulting residue was diluted with H₂O and EPO <DP n="305"/>extracted with 3 x 150 mL CH₂Cl₂. The combined organic fractions were washed with brine and dried over Na₂SO₄ to give i-b (11.7 g, 93percent): MS m/z = 278 (M+H).
13.8 g	at 0 - 20℃; for 39 h;	A solution of 16.1 g of 2-acetylamino-4-iodobenzoic acid (m.p. 233° C.-235° C.; synthesized in accordance with U.S. Pat. No. 4,762,838) in 325 ml of absolute methanol is saturated at 0° C. with dry hydrogen chloride gas. The mixture is heated to the boil for 15 hours, cooled to room temperature, resaturated using dry hydrogen chloride gas, and allowed to stand at room temperature for 24 hours. The solvent is evaporated in vacuo, the residue is taken up in dichloromethane, and the organic phase is washed with a saturated aqueous sodium hydrogen carbonate solution until free from acid. The organic phase is dried over Na₂SO₄, and evaporated in vacuo. This gives 13.8 g of methyl 2-amino-4-iodobenzoate of m.p. 63° C.-67° C.

Reference： [1] Patent: WO2006/41773, 2006, A2, . Location in patent: Page/Page column 303-304
[2] Patent: US2017/121294, 2017, A1, . Location in patent: Paragraph 0058

2
[ 115081-94-2 ]
[ 144550-76-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydroxide In methanol	d. Methyl 2-amino-4-iodobenzoate To a stirred solution of sodium hydroxide (0.048 g, 1.2 mM) in methanol (4.5 mL) was added 7-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (2.6 g, 9.0 mM). The mixture was heated at 60° C. for 7 hr and the resulting solution was cooled, poured into water and extracted with ethyl acetate. The combined extracts were washed once with dilute sodium hydroxide, dried (MgSO₄), filtered and concentrated to leave the title compound (2.0 g, 80percent) as a brown oil which slowly crystallized; MS(CI): 278 (M+H).

Reference： [1] Patent: US5599814, 1997, A,

3
[ 117324-10-4 ]
[ 144550-76-5 ]

Reference： [1] Patent: US5463081, 1995, A,

4
[ 186581-53-3 ]
[ 20776-54-9 ]
[ 144550-76-5 ]

Reference： [1] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7033 - 7036

5
[ 67-56-1 ]
[ 20776-54-9 ]
[ 144550-76-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 16, p. 7671 - 7690

6
[ 144550-76-5 ]
[ 144550-36-7 ]

Reference： [1] Patent: US2017/121294, 2017, A1,

[ 144550-76-5 ] Synthesis Path-Downstream 1~33

1
[ 144550-76-5 ]
[ 1488-42-2 ]
[ 1005029-90-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	copper diacetate; In N,N-dimethyl-formamide; at 20 - 100℃; for 12h;	Diphenyliodonium-2-carboxylate (50) (Fieser, L. F.; Haddadin, M. J. Org. Synth. 1966, 46, 107-112) (0.88 g, 2.72 mmol) and then copper acetate monohydrate (12 mg) are added, at ambient temperature and with moderate stirring, to a solution of <strong>[144550-76-5]methyl 4-iodoanthranilate</strong> (51) (Allison, B. D., Hack, M. D., Phuong, V. K., Rabinowitz, M. H. and Rosen, M. D., U.S. Patent 2005/0038032, 2005) (0.50 g, 1.80 mmol) in dimethylformamide (30 ml). The green mixture obtained is heated at 90-1000C, with stirring, for 12 hours. The solvent is subsequently evaporated under vacuum. Ethyl acetate (18 ml) and then a 0.1N hydrochloric acid solution (18 ml) are successively added to the crude product. The organic phase is then separated by settling and then extracted with a 0.1N aqueous ammonia solution (2 x 9 ml). The aqueous phase recovered is acidified to pH = 6 with a 0.1N hydrochloric acid solution. The mixture is then cooled in an ice bath and then filtered under vacuum. The precipitate obtained is washed with hot water (5 ml). Yield: 80%; melting point: 206-2080C; 1H NMR (400 MHz, J6-DMSO) d 3.83 (s, 3H), 7.04 (t, IH, J = 7.5 Hz), 7.30 (d, IH, J = 8.5 Hz), 7.47 (m, 2H), 7.62 (d, IH, J = 8.5 Hz), 7.74 (s, IH), 7.92 (d, IH, J = 7.5 Hz), 10.70 (s, IH), 13.20 (m, IH); 13C NMR (100 MHz, J6-DMSO) d 52.1, 101.9, 115.6, 118.2 (2C), 121.1, 125.3, 128.5, 131.8, 132.8, 133.5, 142.4, 144.4, 166.5, 168.3; IR (KBr) v cm"1 : 1220, 1254, 1575, 1685, 3000-3600; MS (m/z, %) 397 (M+, 100), 321 (88), 194 (59), 166 (95), 139 (62), 63 (77), 55 (61).

Reference： [1]Patent: WO2008/12782,2008,A2 .Location in patent: Page/Page column 46
[2]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7671 - 7690

2
[ 844646-88-4 ]
[ 144550-76-5 ]
methyl 4-iodo-2-(quinoxaline-5-sulfonylamino)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		C. 4-Iodo-2-(Quinoxaline-5-sulfonylamino)benzoic acid methyl ester. A solution of <strong>[144550-76-5]methyl 2-amino-4-iodobenzoate</strong> (1.2 g, 4.4 mmol), quinoxaline-5-sulfonyl chloride (1.2 g, 5.3 mmol), pyridine (1.7 mL, 22 mmol) and DCM (25 mL) was maintained at 23 C. for 24 h. The reaction mixture was diluted with DCM (200 mL) and washed with satd. aq. NaHCO3, then dried and concentrated to a tan solid. This residue was chromatographed (0 to 100% EtOAc/CH2Cl2) to afford the sulfonamide as a light yellow solid (1.6 g, 77%). MS (ESI): calculated for C16H12IN3O4S, 469.0; m/z found, 470 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 11.10 (s, 1H), 9.07 (d, J=1.8 Hz, 1H), 9.01 (d, J=1.8 Hz, 1H), 8.60 (dd, J=7.4, 1.3 Hz, 1H), 8.40 (dd, J=8.5, 1.3 Hz, 1H), 8.04 (dd, J=7.5, 1.0 Hz, 1H), 7.99 (d, J=1.6 Hz, 1H), 7.51 (d, J=8.3 Hz, 1H), 7.37 (dd, J=8.3, 1.6 Hz, 1H), 3.88 (s, 3H).

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6371 - 6390
[2]Patent: US2005/38032,2005,A1 .Location in patent: Page/Page column 14

3
methyl 2-nitro-4-iodobenzoate [ No CAS ]
[ 144550-76-5 ]

Yield	Reaction Conditions	Operation in experiment
91%		B. Methyl 2-amino-4-iodobenzoate. To a stirred solution of 4-iodo-2-nitrobenzoic acid (2.3 g, 7.9 mmol) in DMF (30 mL) at 0 C. was added DBU (2.4 mL, 16 mmol) followed by iodomethane (1.5 mL, 24 mmol). The reaction mixture was stirred 15 min at 0 C., then was allowed to warm to room temperature and was stirred overnight. The mixture was poured into H2O and extracted with EtOAc (2). The combined organic extracts were washed with H2O (2), dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexanes/EtOAc) to afford methyl 4-iodo-2-nitrobenzoate as a pale yellow solid (2.30 g, 95%). To a solution of the nitrobenzoate (2.3 g, 7.4 mmol) in 1:1 EtOAc/DCM (10 mL) at room temperature was added SnCl2.2H2O (8.3 g, 37 mmol). The reaction mixture was allowed to stir overnight. The solvents were evaporated in vacuo, and the residue was partitioned between satd. aq. NaHCO3 and DCM. The layers were separated, and the aqueous layer was further extracted with DCM (2×). The combined organic layers were dried (MgSO4) and concentrated in vacuo to provide the pure aminobenzoate as a yellow solid (1.87 g, 91%). 1H NMR (500 MHz, CDCl3): 7.52 (d, J=8.5 Hz, 1H), 7.07 (d, J=1.6 Hz, 1H), 6.96 (dd, J=8.5, 1.6 Hz, 1H), 5.72 (br s, 2H), 3.86 (s, 3H).
90%		Step 3: Methyl 2-amino-4-iodobenzoate; To a solution of methyl 4-iodo-2-nitrobenzoate (2.3 g, 7.4 mmol) in DCM (5 mL) and EtOAc(5 mL) was added SnCl2-2H2O (10.8 g, 89.7 mmol). The mixture was allowed to stir for 12 h at rt. The solvents were evaporated, and the residue was partitioned between 200 mL of saturated aqueous NaHCO3 and 200 mL of DCM. The organic solution was separated and the aqueous soluiton was extracted withDCM (2 x 100 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated to give methyl 2-amino-4-iodobenzoate (1.85 g, 90%).

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6371 - 6390
[2]Patent: US2005/38032,2005,A1 .Location in patent: Page/Page column 14
[3]Patent: WO2010/65134,2010,A1 .Location in patent: Page/Page column 58-59

4
[ 144550-76-5 ]
[ 73713-79-8 ]
2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		A. 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodobenzoic acid methyl ester. To a solution of <strong>[144550-76-5]methyl 2-amino-4-iodobenzoate</strong> (EXAMPLE 4, Step B, 1.6 g, 5.8 mmol) in DCM (45 mL) at room temperature was added 4-chlorosulfonyl-2,1,3-benzothiadiazole (1.76 g, 7.51 mmol), and pyridine (0.93 mL, 11 mmol). The mixture was stirred at room temperature overnight, poured into 1 N HCl (200 mL), and extracted with DCM (2*100 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (hexanes/EtOAc) to afford the title sulfonamide as a tan solid (1.87 g, 68%). MS (ESI): calculated for C14H10IN3O4S2, 474.9; m/z found, 474 [M-H]-. 1H NMR (400 MHz, CDCl3): 11.26 (br s, 1H), 8.40 (dd, J=7.0, 1.0 Hz, 1H), 8.24 (dd, J=8.8, 1.0 Hz, 1H), 8.12 (d, J=1.5 Hz, 1H), 7.74 (dd, J=8.8, 7.0 Hz, 1H), 7.53 (d, J=8.5 Hz, 1H), 7.32 (dd, J=8.5, 1.5 Hz, 1H), 3.91 (s, 3H).

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6371 - 6390
[2]Patent: US2005/38032,2005,A1 .Location in patent: Page/Page column 16

6
[ 144550-76-5 ]
[ 144550-77-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sulfur dioxide; sodium nitrite;copper(II) chloride dihydrate; In ice-water; water; acetic acid;	Example 4 Bis (2-methoxycarbonyl-5-iodobenzene)disulfide 13.8 g of <strong>[144550-76-5]methyl 2-amino-4-iodobenzoate</strong> are treated with 48 ml of glacial acetic acid and subsequently with 86 ml of concentrated hydrochloric acid. A solution of 3.8 g of sodium nitrite in 15 ml of water is slowly added dropwise to this suspension which is cooled to -5 C., and stirring is continued at this temperature for 30 minutes. This cooled diazonium salt solution is added dropwise at 0 C. to a solution of 20 ml of sulfur dioxide, 60 ml of glacial acetic acid, 10 ml of water and 3.1 g of copper(II) chloride dihydrate, and stirring is continued first for 1 hour at 0 C. and then overnight at room temperature. The reaction mixture is poured into 1 l of ice-water, and the product is filtered off with suction. This gives 12.7 g of bis(2-methoxycarbonyl-5-iodobenzene)disulfide of m.p. 133-5 C.
12.7 g		13.8 g of <strong>[144550-76-5]methyl 2-amino-4-iodobenzoate</strong> are treated with 48 ml of glacial acetic acid and subsequently with 86 ml of concentrated hydrochloric acid. A solution of 3.8 g of sodium nitrite in 15 ml of water is slowly added dropwise to this suspension which is cooled to -5 C., and stirring is continued at this temperature for 30 minutes. This cooled diazonium salt solution is added dropwise at 0 C. to a solution of 20 ml of sulfur dioxide, 60 ml of glacial acetic acid, 10 ml of water and 3.1 g of copper(II) chloride dihydrate, and stirring is continued first for 1 hour at 0 C. and then overnight at room temperature. The reaction mixture is poured into 1 l of ice-water, and the product is filtered off with suction. This gives 12.7 g of bis(2-methoxycarbonyl-5-iodobenzene)disulfide of m.p. 133 C.-135 C.

Reference： [1]Patent: US5463081,1995,A
[2]Patent: US2017/121294,2017,A1 .Location in patent: Paragraph 0059

7
[ 117324-10-4 ]
[ 144550-76-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; dichloromethane;	Example 3 Methyl 2-amino-4-iodobenzoate A solution of 16.1 g of 2-acetylamino-4-iodobenzoic acid (m.p. 233-5 C.; synthesised in accordance with U.S. Pat. No. 4,762,838) in 325 ml of absolute methanol is saturated at 0 C. with dry hydrogen chloride gas. The mixture is heated to the boil for 15 hours, cooled to room temperature, resaturated using dry hydrogen chloride gas, and allowed to stand at room temperature for 24 hours. The solvent is evaporated in vacuo, the residue is taken up in dichloromethane, and the organic phase is washed with a saturated aqueous sodium hydrogen carbonate solution until free from acid. The organic phase is dried over Na2 SO4, and evaporated in vacuo. This gives 13.8 g of methyl 2-amino-4-iodobenzoate of m.p. 63-7 C.

Reference： [1]Patent: US5463081,1995,A

8
[ 144550-76-5 ]
[ 72287-26-4 ]
[ 2386-64-3 ]
[ 123102-32-9 ]

Yield	Reaction Conditions	Operation in experiment
43.5%	Zinc chloride; In tetrahydrofuran; diethyl ether;	c. Methyl 2-amino-6-ethylbenzoate To a stirred mixture of zinc chloride (8.6 g, 63 mM, previously dried at 200° C. for 2 hr under high vacuum) in tetrahydrofuran (105 mL) under a nitrogen atmosphere was added dropwise a solution of ethyl magnesium chloride (63 mM) in diethyl ether (31.5 mL). After the addition was completed, dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (0.107 g, 0.126 mM) was added to the resulting stirred thick white mixture followed by the dropwise addition of <strong>[144550-76-5]methyl 2-amino-4-iodobenzoate</strong> (3.5 g, 12.6 mM) in tetrahydrofuran (15 mL). The resulting reaction mixture was stirred at room temperature for 2.5 hr and then poured slowly into water (300 mL). The water mixture was extracted with ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated. The residue was chromatographed over silical gel (eluant: Hexanes/diethyl ether; 8.5/1.5) to provide the title ester (1.0 g, 43.5percent) as a pale yellow oil; MS(CI): 180 (M+H). 250-MHz 1 H NMR (DMSO-d6); 7.04 (t, J=7.8, 1H), 6.53 (d, J=8.2, 1H), 6.42 (d, J=7.1, 1H), 5.55 (s, 2H, exchangeable), 3.80 (s, 3H), 2.59 (q, J=7.5, 1H), 1.08 (t, J=7.5, 3H).

Reference： [1]Patent: US5599814,1997,A

9
[ 115081-94-2 ]
[ 144550-76-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydroxide; In methanol;	d. Methyl 2-amino-4-iodobenzoate To a stirred solution of sodium hydroxide (0.048 g, 1.2 mM) in methanol (4.5 mL) was added 7-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (2.6 g, 9.0 mM). The mixture was heated at 60 C. for 7 hr and the resulting solution was cooled, poured into water and extracted with ethyl acetate. The combined extracts were washed once with dilute sodium hydroxide, dried (MgSO4), filtered and concentrated to leave the title compound (2.0 g, 80%) as a brown oil which slowly crystallized; MS(CI): 278 (M+H).

Reference： [1]Patent: US5599814,1997,A

10
[ 144550-76-5 ]
[ 147494-15-3 ]

Yield	Reaction Conditions	Operation in experiment
		e. Dimethyl 7-iodo-4-hydroxyquinoline-2,3-dicarboxylate Using a procedure similar to that described in Example 3c. except starting with <strong>[144550-76-5]methyl 2-amino-4-iodobenzoate</strong>, the crude title diester was obtained as a green solid (2.6 g, 92%). This material was purified by chromatography over silica gel (eluant: methylene chloride/methanol; 9.5/0.5) to provide the title compound (0.85 g, 30%) as a tan solid, mp 243-244 C.; MS(CI): 388 (M+H). Analysis for C13 H10 INO5: Calculated: C, 40.33; H, 2.60; N, 3.62 Found: C, 40.26; H, 2.77; N, 3.54

Reference： [1]Patent: US5599814,1997,A

11
[ 67-56-1 ]
[ 117324-10-4 ]
[ 144550-76-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With thionyl chloride; at 0 - 65℃; for 52h;	To 2-acetylamino-4-iodo-benzoic acid (13.8 g, 45.3 mmol) in 200 mL of dry methanol was added SOCl2 (32.7 mL, 453 mmol) dropwise at 0 C. The reaction mixture was then heated at 65 C for 2 h. The reaction was then cooled to 0 C, an additional portion of SOCl2 (10 mL, 137 mmol) was added, and the reaction was heated at 65 0C for 2 h. The reaction was then cooled to 0 C, a final portion of SOCl2 (10 mL, 137 mmol) was added, and the reaction was heated at 65 C for 48 h. The reaction was then cooled to 22 C and concentrated in vacuo The resulting residue was diluted with H2O and EPO <DP n="305"/>extracted with 3 x 150 mL CH2Cl2. The combined organic fractions were washed with brine and dried over Na2SO4 to give i-b (11.7 g, 93%): MS m/z = 278 (M+H).
13.8 g	With hydrogenchloride; at 0 - 20℃; for 39h;	A solution of 16.1 g of 2-acetylamino-4-iodobenzoic acid (m.p. 233 C.-235 C.; synthesized in accordance with U.S. Pat. No. 4,762,838) in 325 ml of absolute methanol is saturated at 0 C. with dry hydrogen chloride gas. The mixture is heated to the boil for 15 hours, cooled to room temperature, resaturated using dry hydrogen chloride gas, and allowed to stand at room temperature for 24 hours. The solvent is evaporated in vacuo, the residue is taken up in dichloromethane, and the organic phase is washed with a saturated aqueous sodium hydrogen carbonate solution until free from acid. The organic phase is dried over Na2 SO4, and evaporated in vacuo. This gives 13.8 g of methyl 2-amino-4-iodobenzoate of m.p. 63 C.-67 C.

Reference： [1]Patent: WO2006/41773,2006,A2 .Location in patent: Page/Page column 303-304
[2]Patent: US2017/121294,2017,A1 .Location in patent: Paragraph 0058

12
[ 67-56-1 ]
[ 20776-54-9 ]
[ 144550-76-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7671 - 7690

13
[ 144550-76-5 ]
[ 1490-25-1 ]
[ 1228960-81-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	Example 2:Synthesis of compounds of formula iv; 8-iodo-3,4-dihvdro-lH-l-benzazepine-2,5-dione; Step 1 : Methyl 4-iodo-2-[(4-methoxy-4-oxobutanoyl)amino]benzoate; To a solution of <strong>[144550-76-5]methyl 2-amino-4-iodobenzoate</strong> (17 g, 61.3 mmol) in DCM (200 mL), was added DIEA (10.6 mL, 64.4 mmol) and DMAP (37.5 mg, 0.31 mmol). To this solution was added 3- (carbomethoxy)propionyl chloride (8.3 mL, 67.4 mmol) dropwise, and the reaction mixture was allowed to stir at rt for 2 h. To the reaction mixture was then added H2O (80 mL) and the mixture was allowed to stir for 30 min. The organic solution was separated and the aqueous solution was extracted with DCM (2 x 100 mL). The organic solutions were combined, washed with H2O (2 x 100 mL) and brine (1 x 100 mL), dried over Na2SO4, filtered and concentrated to give methyl 4-iodo-2-[(4-methoxy-4- oxobutanoyl)amino]benzoate (24.6 g, 99%).

Reference： [1]Patent: WO2010/65134,2010,A1 .Location in patent: Page/Page column 61
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 197 - 208

14
[ 186581-53-3 ]
[ 20776-54-9 ]
[ 144550-76-5 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7033 - 7036

15
[ 144550-76-5 ]
[ 100-52-7 ]
[ 1246775-81-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7033 - 7036

16
[ 144550-76-5 ]
[ 100-52-7 ]
[ 1029-88-5 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7033 - 7036

17
[ 144550-76-5 ]
[ 884197-15-3 ]