Oxalyl chloride → HCID 178464524, compound

HRID 926053Notes

Reaction equation

HRID 926053 reaction equation
[CH2:1]([N:3]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17]1)[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11])(=[O:6])=[O:5])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH2:32][C:33]1[S:34][C:35]2[CH2:62][CH2:61][CH2:60][CH2:59][C:36]=2[C:37]=1[C:38]([NH:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][C:49]2[CH:58]=[CH:57][C:52]([C:53]([O:55][CH3:56])=[O:54])=[CH:51][CH:50]=2)=[CH:43][CH:42]=1)=[O:39]>CN(C=O)C.ClCCl.N1C=CC=CC=1>[CH2:1]([N:3]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17]1)[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([NH:32][C:33]1[S:34][C:35]2[CH2:62][CH2:61][CH2:60][CH2:59][C:36]=2[C:37]=1[C:38]([NH:40][C:41]1[CH:42]=[CH:43][C:44]([CH2:47][CH2:48][C:49]2[CH:50]=[CH:51][C:52]([C:53]([O:55][CH3:56])=[O:54])=[CH:57][CH:58]=2)=[CH:45][CH:46]=1)=[O:39])=[O:11])(=[O:6])=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 68207883Methyl 4-[2-(4-{[(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoateHCID 178464526HCID 178464526, compound

Product 1

HCID 178464524HCID 178464524, compoundYield 70.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 319 mg of 3-{ethyl[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoic acid, 0.10 mL of oxalyl chloride, 2.5 mL of dichloromethane, and one drop of DMF was stirred at room temperature for 2 hours, and then the reaction mixture was concentrated under reduced pressure. A mixture of the obtained crude product and 2.5 mL of dichloromethane was added to a mixture of 0.050 mL of pyridine, 250 mg of methyl 4-[2-(4-{[(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate, and 2.5 mL of dichloromethane, followed by stirring at room temperature overnight. The reaction mixture was purified by silica gel column chromatography (hexane-chloroform) to obtain 320 mg of methyl 4-(2-{4-[({2-[(3-{ethyl[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate as a yellow foamed solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionA mixture of the
  3. customobtained crude product and 2.5 mL of dichloromethane
  4. stirringby stirring at room temperature overnight
  5. customThe reaction mixture was purified by silica gel column chromatography (hexane-chloroform)

Sources & evidence

ORD record
ord-eed63bc3730d403ba970f284b4fe4773
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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