Cyclopropanemethanamine → N-tert-Butyl-3-((4-(4-(3-(cyclopropylmethyl)ureido)-2-fluorobenzoyl)piperazin-1-yl)methyl)benzamide

HRID 1878343ノート

反応式

HRID 1878343 の反応式
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[NH2:14][C:15]1[CH:42]=[CH:41][C:18]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:29]=[C:30]([CH:38]=[CH:39][CH:40]=3)[C:31]([NH:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:23][CH2:22]2)=[O:20])=[C:17]([F:43])[CH:16]=1.[CH:44]1([CH2:47][NH2:48])[CH2:46][CH2:45]1>C(#N)C>[C:34]([NH:33][C:31](=[O:32])[C:30]1[CH:38]=[CH:39][CH:40]=[C:28]([CH2:27][N:24]2[CH2:25][CH2:26][N:21]([C:19](=[O:20])[C:18]3[CH:41]=[CH:42][C:15]([NH:14][C:2]([NH:48][CH2:47][CH:44]4[CH2:46][CH2:45]4)=[O:3])=[CH:16][C:17]=3[F:43])[CH2:22][CH2:23]2)[CH:29]=1)([CH3:37])([CH3:36])[CH3:35]

参加物

5

反応物 3

HCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 579176473-((4-(4-Amino-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

生成物 1

HCID 57917593N-tert-Butyl-3-((4-(4-(3-(cyclopropylmethyl)ureido)-2-fluorobenzoyl)piperazin-1-yl)methyl)benzamide収率 8.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4-Nitrophenyl chloroformate (59 mg, 0.29 mmol) was added to a solution of 3-((4-(4-amino-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tertbutylbenzamide (100 mg, 0.24 mmol) in acetonitrile (10 mL). After stirring at room temperature for 1 hour, cyclopropylmethylamine (126 μL, 1.21 mmol) was added. After 2 hours stirring, the reaction was purified by strong cation exchange chromatography, eluting macroporous polystyrene sulfonic acid with 2N ammonia in methanol. The resulting solution was concentrated under vacuum and purified by basic reverse phase HPLC to afford the title compound as a white solid (10 mg).

後処理

  1. stirringAfter 2 hours stirring
  2. customthe reaction was purified by strong cation exchange chromatography
  3. washeluting macroporous polystyrene sulfonic acid with 2N ammonia in methanol
  4. concentrationThe resulting solution was concentrated under vacuum
  5. custompurified by basic reverse phase HPLC

出典と根拠

ORDレコード
ord-e3eb9176b36346c1a72d1df8eb0f5c65
出典データセット
uspto-grants-2012_11
特許番号
US08314091B2

反応ノート

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