2-Cyclohexyloxy-5-methanesulfonyl-benzoic acid → 2-[4-(2-Cyclohexyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-thiazole-5-carbonitrile

HRID 1352296Notes

Reaction equation

HRID 1352296 reaction equation
[CH:1]1([O:7][C:8]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:9]=2[C:10]([OH:12])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:21]1([C:27]2[S:28][C:29]([C:32]#[N:33])=[CH:30][N:31]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>>[CH:1]1([O:7][C:8]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:9]=2[C:10]([N:24]2[CH2:25][CH2:26][N:21]([C:27]3[S:28][C:29]([C:32]#[N:33])=[CH:30][N:31]=3)[CH2:22][CH2:23]2)=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 211002212-Cyclohexyloxy-5-methanesulfonyl-benzoic acidHCID 211002572-Piperazin-1-yl-thiazole-5-carbonitrile

Product 1

HCID 211002092-[4-(2-Cyclohexyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-thiazole-5-carbonitrileYield 49%

Procedure

Prepared in analogy to example 1 (b) from 2-cyclohexyloxy-5-methanesulfonyl-benzoic acid (Example A7) and 2-piperazin-1-yl-thiazole-5-carbonitrile (Example 6(a)). The crude material was purified by chromatography (SiO2, ethyl acetate/heptane) followed by trituration in ether to yield the title compound as a white crystalline solid (yield 49%). MS (m/e): 475.4 (M+H+, 100%).

Workup

  1. customThe crude material was purified by chromatography (SiO2, ethyl acetate/heptane)

Sources & evidence

ORD record
ord-a885b40979f74bb3a237055454e70198
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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