HCID 86079888, compound → HCID 178461401, compound

HRID 1162560Notes

Reaction equation

HRID 1162560 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:12]([NH2:14])=[S:13])=[CH:6][CH:5]=1.Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH:32]2[CH2:37][CH2:36][CH:35]([CH3:38])[CH2:34][CH2:33]2)=[CH:27][CH:26]=1)=O>>[CH:15]1([N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:20])=[CH:5][CH:6]=2)[C:12]2[S:13][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C@H:32]4[CH2:37][CH2:36][C@@H:35]([CH3:38])[CH2:34][CH2:33]4)=[CH:27][CH:26]=3)[N:14]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 86079888HCID 86079888, compoundHCID 86601762HCID 86601762, compound

Product 1

HCID 178461401HCID 178461401, compoundYield 36.7%

Procedure

4-[(Cyclopentyl-{4-[4-(cis-4-methyl-cyclohexyloxy)-phenyl]-thiazol-2-yl}-amino)-methyl]-benzoic acid (90 mg) was prepared following procedure B using 4-[(1-cyclopentyl-thioureido)-methyl]-benzoic acid methyl ester (150 mg, 0.5 mmol) and 2-bromo-1-[4-(4-methyl-cyclohexyloxy)-phenyl]-ethanone (0.5 mmol). Purification (Silica gel, ethyl acetate/hexane 5:95) provided the ester, which was hydrolyzed following procedure T. Sodium 4-[(cyclopentyl-{4-[4-(cis-4-methyl-cyclohexyloxy)-phenyl]-thiazol-2-yl}-amino)-methyl]-benzoate was made following procedure J. LCMS m/z: 492 (M+1)+.

Workup

  1. customPurification (Silica gel, ethyl acetate/hexane 5:95)

Sources & evidence

ORD record
ord-c536f391091a42d39273aa7d1f36cf29
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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