Diisopropylcarbodiimide → 2-Phenoxymethyl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole-5-carboxylic acid 4-methoxy-benzylamide

HRID 507203Notes

Reaction equation

HRID 507203 reaction equation
[O:1]([CH2:8][C:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C:12]2[CH:26]=[CH:27][C:28]([C:30]([OH:32])=O)=[CH:29][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)N=C=NC(C)C.[CH3:42][O:43][C:44]1[CH:51]=[CH:50][C:47]([CH2:48][NH2:49])=[CH:46][CH:45]=1>C1COCC1>[CH3:42][O:43][C:44]1[CH:51]=[CH:50][C:47]([CH2:48][NH:49][C:30]([C:28]2[CH:27]=[CH:26][C:12]3[N:13]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:25])[F:24])=[CH:17][CH:16]=4)[C:9]([CH2:8][O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:10][C:11]=3[CH:29]=2)=[O:32])=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 754524-MethoxybenzylamineHCID 684638462-phenoxymethyl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole-5-carboxylic acid

Product 1

HCID 684654132-Phenoxymethyl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole-5-carboxylic acid 4-methoxy-benzylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.16 mmol of 2-phenoxymethyl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole-5-carboxylic acid were dissolved in 1 ml THF with 1 eq. DIC. After 15 min 1.5 eq of 4-methoxy-benzylamine were added and the reaction stirred at room temperature for 16 h. The crude material was purified via reversed phase preparative HPLC. MS(ISP): 562.3 (M+H)+.

Workup

  1. customThe crude material was purified via reversed phase preparative HPLC

Sources & evidence

ORD record
ord-ee71102eb0b045b8bfec93c0b81f46be
Source dataset
uspto-grants-2010_08
Patent number
US07786128B2

Reaction notes

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