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 1748345Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-50395783363f46f5adc43210fb01452e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150577B2

Reaction notes

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