Triethylamine → N-[(2S,6R)-4-(Cyclopropylmethyl)-5-oxo-2-phenyl-1,4-oxazepan-6-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide

HRID 493665

반응식

HRID 493665 반응식
C(N(CC)CC)C.[NH2:8][C@@H:9]1[CH2:15][O:14][C@@H:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][N:11]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:10]1=[O:26].Cl[C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29].C(N(C(C)C)CC)(C)C.Cl.Cl.[O:51]=[C:52]1[NH:60][C:55]2=[N:56][CH:57]=[CH:58][CH:59]=[C:54]2[N:53]1[CH:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1>O1CCCC1.ClCCl>[CH:23]1([CH2:22][N:11]2[C:10](=[O:26])[C@H:9]([NH:8][C:28]([N:64]3[CH2:65][CH2:66][CH:61]([N:53]4[C:54]5[C:55](=[N:56][CH:57]=[CH:58][CH:59]=5)[NH:60][C:52]4=[O:51])[CH2:62][CH2:63]3)=[O:29])[CH2:15][O:14][C@@H:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12]2)[CH2:25][CH2:24]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 60037869(2S,6R)-6-amino-4-(cyclopropylmethyl)-2-phenyl-1,4-oxazepan-5-one

생성물 1

HCID 11283500N-[(2S,6R)-4-(Cyclopropylmethyl)-5-oxo-2-phenyl-1,4-oxazepan-6-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide수율 85.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (0.015 mL, 0.109 mmol) was added to a solution of (2S,6R)-6-amino-4-(cyclopropylmethyl)-2-phenyl-1,4-oxazepan-5-one (27 mg, 0.104 mmol) and 4-nitrophenyl chloroformate (22 mg, 0.109 mmol) in tetrahydrofuran (2 mL) at 0° C. After 0.5 h, diisopropylethylamine (0.072 mL, 0.415 mmol), 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride (36 mg, 0.124 mmol), and dichloromethane (2.5 mL) were added and the mixture warmed to ambient temperature. After 18 h, the mixture was concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (45 mg). MS 505.2559 (M+1).

후처리

  1. waitAfter 18 h
  2. concentrationthe mixture was concentrated
  3. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-912928c76cb1459aba0a4f84592a9e8b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534784B2

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