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 20156

反応式

HRID 20156 の反応式
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

参加物

8

反応物 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

生成物 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-carboxamide収率 85.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7f4610bd0f7043ccb422dfb89a9be381
出典データセット
uspto-grants-2010_06
特許番号
US07745427B2

関連ノート

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