4-Methoxybenzylamine → 4-[5-(2-(4-Methoxybenzylamino)-pyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid benzyl ester

HRID 342691Notes

Reaction equation

HRID 342691 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[NH:18][C:19]([C:32]3[CH:37]=[CH:36][N:35]=[C:34](S(C)(=O)=O)[N:33]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:42][O:43][C:44]1[CH:51]=[CH:50][C:47]([CH2:48][NH2:49])=[CH:46][CH:45]=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[NH:18][C:19]([C:32]3[CH:37]=[CH:36][N:35]=[C:34]([NH:49][CH2:48][C:47]4[CH:50]=[CH:51][C:44]([O:43][CH3:42])=[CH:45][CH:46]=4)[N:33]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 754524-MethoxybenzylamineHCID 106748344-[5-(2-Methylsulfonylpyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 158406444-[5-(2-(4-Methoxybenzylamino)-pyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid benzyl esterYield 92.4%

Conditions

Temperature
140 °C

Procedure

A mixture of 4-[5-(2-methylsulfonylpyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid benzyl ester (1.5 g, 0.00256 mole) and 4-methoxybenzylamine (3.51 g, 0.026 mole) was heated in a pressure tube at 140° C. for 10 minutes. The mixture was allowed to cool and the residue column chromatographed on silica using 5% methanol/methylene chloride to give 1.52 g of a yellow powder upon concentration in vacuo of product containing fractions.

Workup

  1. temperatureto cool
  2. customthe residue column chromatographed on silica using 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-24b96c9b5242449f8c9502e49f6cab6d
Source dataset
uspto-grants-1999_01
Patent number
US05859041

Reaction notes

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