Dimethylformamide → Cyclohexanecarboxamide

HRID 410549

반응식

HRID 410549 반응식
[Cl-].[NH4+].CN(C(ON1N=N[C:13]2[CH:14]=[CH:15][CH:16]=[N:17][C:12]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N([CH:33]([CH3:35])C)CC)(C)C.CN(C)C=[O:39]>O>[CH:13]1([C:12]([NH2:17])=[O:39])[CH2:14][CH2:15][CH2:16][CH2:35][CH2:33]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 14283Cyclohexanecarboxamide수율 88%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

cis-4-Hydroxy-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylic acid (500 mg, 1.05 mmol), ammonium chloride (112 mg, 2.09 mmol), 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (795 mg, 2.09 mmol), and diisopropylethylamine (730 μl, 4.18 mmol) were taken-up in dimethylformamide (4.2 mL) under argon. The vessel was sealed and stirred at 65° C. for 4 hours. Upon cooling, the reaction mixture was diluted with water, and the resulting precipitate was collected via filtration. The solids were washed with water and diethyl ether and dried in vacuo overnight to afford cis-4-hydroxy-4-[5-(3-methyl-5-{[4-Orifluoromethyl)pyrimidin-2-yl]amino}-phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxamide (437.6 mg, 0.916 mmol, 88% yield) as a white solid. MS ESI: [M+H]+ m/z 478.1.

후처리

  1. customThe vessel was sealed
  2. temperatureUpon cooling
  3. filtrationthe resulting precipitate was collected via filtration
  4. washThe solids were washed with water and diethyl ether
  5. customdried in vacuo overnight

출처 및 근거

ORD 기록
ord-55a704798d9848d4a5415133f0b7ea22
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759366B2

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