Pyridine → N-(5-benzyl-1,2-oxazol-3-yl)-10-methyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxamide

HRID 1521765ノート

反応式

HRID 1521765 の反応式
[CH3:1][CH:2]1[N:8]2[C:9]3[N:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][C:10]=3[CH:11]=[C:7]2[C:6](=[O:19])[NH:5][CH2:4][CH2:3]1.ClC(N(C)C)=C(C)C.[CH2:28]([C:35]1[O:39][N:38]=[C:37]([NH2:40])[CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N1C=CC=CC=1>C(Cl)Cl>[CH2:28]([C:35]1[O:39][N:38]=[C:37]([NH:40][C:16]([C:14]2[CH:13]=[CH:12][C:10]3[CH:11]=[C:7]4[C:6](=[O:19])[NH:5][CH2:4][CH2:3][CH:2]([CH3:1])[N:8]4[C:9]=3[N:15]=2)=[O:18])[CH:36]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 672354765-Benzylisoxazol-3-amine2 回HCID 6723721510-Methyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid2 回

生成物 1

HCID 53242177N-(5-benzyl-1,2-oxazol-3-yl)-10-methyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxamide収率 16%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 10-methyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3′,2′:4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid (Intermediate G, 75 mg, 0.29 mmol) in CH2Cl2 (5 mL) is added 1-chloro-N,N,2-trimethylpropenylamine (138 μL, 1.01 mmol) and the mixture is stirred at room temperature for 30 min. 5-benzyl-1,2-oxazol-3-amine (Intermediate W, 252 mg, 1.45 mmol) and pyridine (94 μL, 1.16 mmol) are added and the reaction is stirred at room temperature for 20 h. The mixture is concentrated under reduced pressure and the residue is purified via preparative HPLC using a gradient elution from 10-90% acetonitrile/H2O with 0.1% TFA to afford the title compound (19 mg, 16%). LCMS: 416.20 (M+H+). (System V-med polar)

後処理

  1. stirringthe reaction is stirred at room temperature for 20 h
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customthe residue is purified via preparative HPLC
  4. washa gradient elution from 10-90% acetonitrile/H2O with 0.1% TFA

出典と根拠

ORDレコード
ord-d3f4fcd682a0418a806131ab6a17224d
出典データセット
uspto-grants-2015_07
特許番号
US09073926B2

反応ノート

読み込み中…