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 1521765노트

반응식

HRID 1521765 반응식
[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

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 672354765-Benzylisoxazol-3-amine2회HCID 6723721510-Methyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid2회

생성물 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-carboxamide수율 16%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-d3f4fcd682a0418a806131ab6a17224d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073926B2

반응 노트

불러오는 중…