Pyridine → HCID 24657609, compound

HRID 1162593Notes

Reaction equation

HRID 1162593 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:20](Cl)=[O:21])[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:20]([CH:16]3[CH2:19][CH2:18][CH2:17]3)=[O:21])[S:13][CH:14]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 78705Cyclobutanecarbonyl chlorideHCID 6736934-(4-Isopropyl-phenyl)-thiazol-2-ylamine

Product 1

HCID 24657609HCID 24657609, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Isopropyl-phenyl)-thiazol-2-yl amine (90 mg, 0.41 mmol) was acylated in CH2Cl2 using cyclobutane carbonyl chloride (60 μL, 0.52 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 95 mg (80%) of cyclobutanecarboxylic 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-620e103ccd1c42cda0b324d78670dd83
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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