Diisopropylamine → 4-Benzimidazol-1-yl-piperidine-1-carboxylic acid 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl Ester

HRID 1179978Notes

Reaction equation

HRID 1179978 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)=[CH:7][CH:6]=1)=[O:3].[NH:22]1[CH2:27][CH2:26][CH:25]([N:28]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[N:30]=[CH:29]2)[CH2:24][CH2:23]1.C(NC(C)C)(C)C>>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([O:4][C:2]([N:22]3[CH2:23][CH2:24][CH:25]([N:28]4[C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=5[N:30]=[CH:29]4)[CH2:26][CH2:27]3)=[O:3])=[CH:6][CH:7]=2)=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 7912DiisopropylamineHCID 30192621-(4-Piperidinyl)-1H-benzimidazoleHCID 220477624-(5-Trifluoromethylpyridin-2-yloxy)-phenyl chloroformate

Product 1

HCID 695178894-Benzimidazol-1-yl-piperidine-1-carboxylic acid 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl Ester

Procedure

The crude product was prepared from 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate and 1-piperidine-4-yl-1H-benzimidazole, 5 equivalent of diisopropylamine was added, preparative HPLC (method C) (23%, colourless crystals). HPLC-MS m/z=483.3 (M+1), Rt: 3.14 min.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-dcc0e3de853d46eca584c1b60bb21762
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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