Triphosgene → N-(1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-yl)-4-(6-methylpyridin-2-yl)piperazine-1-carboxamide

HRID 535780노트

반응식

HRID 535780 반응식
ClC(O[C:6](=[O:12])OC(Cl)(Cl)Cl)(Cl)Cl.Cl.[NH2:14][CH:15]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:16]([C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)=[O:17].[CH3:30][C:31]1[N:36]=[C:35]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[C:22]([C:21]1[CH:24]=[CH:25][C:18]([C:16](=[O:17])[CH:15]([NH:14][C:6]([N:40]2[CH2:41][CH2:42][N:37]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([CH3:30])[N:36]=3)[CH2:38][CH2:39]2)=[O:12])[C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:19][CH:20]=1)#[N:23]

참가 물질

5

반응물 3

HCID 94429TriphosgeneHCID 27369461-(6-Methylpyridin-2-yl)piperazineHCID 682779744-(2-Amino-3,3-dimethylbutanoyl)benzonitrile hydrochloride

생성물 1

HCID 56961883N-(1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-yl)-4-(6-methylpyridin-2-yl)piperazine-1-carboxamide수율 90.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Bis(trichloromethyl)carbonate (60.6 mg, 0.20 mmol) was added portion-wise to 4-(2-amino-3,3-dimethylbutanoyl)benzonitrile hydrochloride (Example 3, 129 mg, 0.51 mmol) and TEA (0.285 mL, 2.04 mmol) in DCM (2 mL) under 1 minute at rt. After stirring for 20 min, a solution of 1-(6-methylpyridin-2-yl)piperazine (CAS 55745-89-6, 90 mg, 0.51 mmol) and TEA (0.142 mL, 1.02 mmol) in DCM (2 mL) was added drop-wise and the reaction was stirred for 90 min. The volatiles were removed before the reaction mixture was diluted with MeOH, filtered and purified by preparative HPLC. Fractions were pooled and freeze-dried to give N-(1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-yl)-4-(6-methylpyridin-2-yl)piperazine-1-carboxamide (76 mg, 36%).

후처리

  1. stirringthe reaction was stirred for 90 min
  2. customThe volatiles were removed before the reaction mixture
  3. additionwas diluted with MeOH
  4. filtrationfiltered
  5. custompurified by preparative HPLC
  6. customfreeze-dried

출처 및 근거

ORD 기록
ord-b50ec146161044809f5c535770aa5008
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859556B2

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