Nitrogen → 4-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamide

HRID 1748345노트

반응식

HRID 1748345 반응식
[CH3:1][CH:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([OH:17])=O)[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[CH3:40][C:41]1[O:45][N:44]=[C:43]([NH2:46])[CH:42]=1.C(N(CC)C(C)C)(C)C.N#N>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:1][CH:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([NH:46][C:43]4[CH:42]=[C:41]([CH3:40])[O:45][N:44]=4)=[O:17])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1

참가 물질

9

반응물 6

HCID 947NitrogenHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 661723-Amino-5-methylisoxazoleHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 587675714-Methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid

생성물 1

HCID 672349974-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamide수율 48%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid (50 mg, 0.21 mmol) in DMF (1 mL) are added N-hydroxybenzotriazole (39 mg, 0.29 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (61 mg, 0.32 mmol). After stirring for 10 min, 5-methyl-3-aminoisoxazole (38 mg, 0.39 mmol), N,N-diisopropylethylamine (0.07 mL, 0.42 mmol) and 4-dimethylaminopyridine (2.6 mg, 0.02 mmol) are added. The reaction mixture is heated at 50° C. for 15 h and simultaneously a stream of N2 is blown over the reaction mixture to remove DMF. The residue is cooled to room temperature and EtOAc (4 mL) and water (2 mL) are added. The resulting white solid is collected by filtration to afford the title compound (32 mg, 48%). LCMS (ESMS): m/z 325.61 (M+H+).

후처리

  1. customto remove DMF
  2. temperatureThe residue is cooled to room temperature
  3. additionEtOAc (4 mL) and water (2 mL) are added
  4. filtrationThe resulting white solid is collected by filtration

출처 및 근거

ORD 기록
ord-50395783363f46f5adc43210fb01452e
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

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