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 1748345ノート

反応式

HRID 1748345 の反応式
[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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-50395783363f46f5adc43210fb01452e
出典データセット
uspto-grants-2015_10
特許番号
US09150577B2

反応ノート

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