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

HRID 535780ノート

反応式

HRID 535780 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b50ec146161044809f5c535770aa5008
出典データセット
uspto-grants-2014_10
特許番号
US08859556B2

反応ノート

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