Triethylamine → tert-Butyl 4-(4-(3-(2-amino-2-methylpropyl)ureido)-3-fluorobenzyl)piperidine-1-carboxylate

HRID 515295노트

반응식

HRID 515295 반응식
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[F:22].Cl[C:24](OC1C=CC([N+]([O-])=O)=CC=1)=[O:25].[CH3:36][C:37]([NH2:41])([CH3:40])[CH2:38][NH2:39].C(N(CC)CC)C>O1CCCC1>[NH2:41][C:37]([CH3:40])([CH3:36])[CH2:38][NH:39][C:24](=[O:25])[NH:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH2:11][CH2:12]2)=[CH:4][C:3]=1[F:22]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 821294-Nitrophenyl chloroformateHCID 67193052Tert-butyl 4-(4-amino-3-fluorobenzyl)piperidine-1-carboxylate

생성물 1

HCID 86670947tert-Butyl 4-(4-(3-(2-amino-2-methylpropyl)ureido)-3-fluorobenzyl)piperidine-1-carboxylate수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

tert-Butyl 4-(4-amino-3-fluorobenzyl)piperidine-1-carboxylate (3.44 mmol, 1.06 g) and 4-nitrophenyl chloroformate (3.44 mmol, 0.693 g) were combined in tetrahydrofuran (5 mL) and the reaction stirred at room temperature for 1 hour. 2-Methylpropane-1,2-diamine (3.44 mmol, 0.303 g) and triethylamine (10.31 mmol, 1.043 g) were added and the mixture stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue purified by silica gel column chromatography (eluting with dichloromethane to 20% methanol/dichloromethane) to afford the title compound (960 mg). MS (ESI) m/z 423.2 [M+H]+

후처리

  1. stirringthe mixture stirred at room temperature overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue purified by silica gel column chromatography (eluting with dichloromethane to 20% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-46e7ad5f7586464a8fef1c688ae03645
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108939B2

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