4-(Trifluoromethyl)phenyl isocyanate → 1-{3-[4-(2-aminopyrimidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)phenyl]urea

HRID 45877노트

반응식

HRID 45877 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)=[CH:11][N:10]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:36]=[CH:35][C:34]([N:37]=[C:38]=[O:39])=[CH:33][CH:32]=1.[Na]>CN(C)C=O>[NH2:19][C:15]1[N:14]=[C:13]([C:12]2[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:38]([NH:37][C:34]4[CH:33]=[CH:32][C:31]([C:30]([F:29])([F:40])[F:41])=[CH:36][CH:35]=4)=[O:39])[CH:7]=[CH:6][CH:5]=3)=[N:9][N:10]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[CH:11]=2)[CH:18]=[CH:17][N:16]=1

참가 물질

5

반응물 3

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 5360545SodiumHCID 671841854-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyrimidin-2-amine

생성물 1

HCID 671848701-{3-[4-(2-aminopyrimidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)phenyl]urea수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1 g (2.7 mmol) of 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-pyrimidin-2-amine was dissolved in 290 ml of dry dimethylformamide and 386 μl of p-trifluoromethyl-phenylisocyanate were added. The reaction was then stirred at room temperature overnight. The mixture was poured into aqueous sodium hydrogenocarbonate and extracted with dichloromethane. The organic layer was then dried over sodium sulphate and evaporated. The crude was purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 8/2), affording 800 mg (53%) of the title compound.

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was then dried over sodium sulphate
  3. customevaporated
  4. customThe crude was purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 8/2)

출처 및 근거

ORD 기록
ord-3945bfe004424d1c8f822561ea36dce0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541575B2

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