Water → HCID 58706380, compound

HRID 2114173Notes

Reaction equation

HRID 2114173 reaction equation
N[C:2]1([NH:35][CH:36]([CH3:38])[CH3:37])[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][CH:3]1[NH:16][C:17]([C:19]1[C:20]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:18].C(N(CC)CC)C.[Cl:46][CH2:47][C:48](Cl)=[O:49].O>C(Cl)(Cl)Cl>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([NH:16][C:17]([C:19]2[C:20]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][CH:26]=3)=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:18])=[C:2]([N:35]([C:48](=[O:49])[CH2:47][Cl:46])[CH:36]([CH3:38])[CH3:37])[CH:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 86607645HCID 86607645, compound

Product 1

HCID 58706380HCID 58706380, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4′-trifluoromethylbiphenyl-2-carboxylic acid (2-amino-4-benzyloxy-2-isopropylaminophenyl)amide (140 mg) and triethylamine (42 mg) in chloroform was added chloroacetyl chloride (48 mg) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. After addition of water to the reaction solution, it is extracted with chloroform. The extract was dried over sodium sulfate and then concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give 4′-trifluoromethylbiphenyl-2-carboxylic acid {4-benzyloxy-2-[(2-chloroacetyl)isopropylamino]phenyl}amide (140 mg).

Workup

  1. temperaturecooling
  2. extractionis extracted with chloroform
  3. dry with materialThe extract was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-d2017f238d74458ca805319d0dbb34c3
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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