Dimethylformamide → Cyclohexanecarboxamide

HRID 410549

反応式

HRID 410549 の反応式
[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

参加物

6

反応物 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)

生成物 1

HCID 14283Cyclohexanecarboxamide収率 88%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-55a704798d9848d4a5415133f0b7ea22
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

関連ノート

読み込み中…