Pyridine → Cyclohexanecarboxylic acid [4-(4-isopropyl-phenyl)-thiazol-2-yl]-amide

HRID 1162594Notes

Reaction equation

HRID 1162594 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH2:15])[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH:16]1([C:22](Cl)=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.N1C=CC=CC=1>C(Cl)Cl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([NH:15][C:22]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:23])[S:13][CH:14]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 75938Cyclohexanecarbonyl chlorideHCID 6736934-(4-Isopropyl-phenyl)-thiazol-2-ylamine

Product 1

HCID 3590092Cyclohexanecarboxylic acid [4-(4-isopropyl-phenyl)-thiazol-2-yl]-amideYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Isopropyl-phenyl)-thiazol-2-yl amine (100 mg, 0.46 mmol) was acylated in CH2Cl2 using cyclohexane carbonyl chloride (85 μL, 0.57 mmol, 1.25 eq.) in the presence of excess pyridine. The reaction was quenched with sat. NH4Cl, extracted with EtOAc and dried over MgSO4. Purification by silica gel chromatography (10% EtOAc in hexanes) afforded 123 mgs cyclohexanecarboxylic acid [4-(4-isopropyl-phenyl)-thiazol-2-yl]-amide.

Workup

  1. customThe reaction was quenched with sat. NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customPurification by silica gel chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-87634a6976b44bf69b646f6e9be571c5
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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