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

HRID 515295ノート

反応式

HRID 515295 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+

後処理

  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)

出典と根拠

ORDレコード
ord-46e7ad5f7586464a8fef1c688ae03645
出典データセット
uspto-grants-2015_08
特許番号
US09108939B2

反応ノート

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