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

HRID 1878343노트

반응식

HRID 1878343 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e3eb9176b36346c1a72d1df8eb0f5c65
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314091B2

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