Ethylenediamine → 2-(1H-indol-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246439Notes

Reaction equation

C([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[CH:22]4)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])(C)(C)C.C(N)CN>CN(C=O)C.O>[NH:24]1[C:25]2[C:21](=[CH:20][CH:19]=[CH:18][C:17]=2[C:14]2[N:15]=[C:16]3[C:8]([C:6]([NH2:5])=[O:7])=[CH:9][NH:10][C:11]3=[N:12][CH:13]=2)[CH:22]=[CH:23]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of N-tert-butyl-2-(1H-indol-7-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (54 mg, 116 μmol) in DMF (3 mL) was added ethylenediamine (350 mg, 393 μL, 5.82 mmol) and the mixture heated at 60° C. After 72 h, the reaction mixture was cooled, diluted with water, and extracted into ethyl acetate. The organic phases were combined and washed with water and brine then dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with ether, then water, diluted with dichloromethane, and finally the solvents removed in vacuo to give N-tert-butyl-2-(2-(1H-indol-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (14 mg). MS (M+H)+=334.1; 1H NMR (DMSO-d6) δ: 12.83 (br. s., 1H), 11.46 (br. s., 1H), 9.01 (s, 1H), 8.49 (s, 1H), 8.24 (s, 1H), 7.81 (d, J=7.8 Hz, 1H), 7.73 (d, J=7.5 Hz, 1H), 7.52 (br. s., 1H), 7.30 (t, J=7.5 Hz, 1H), 6.69 (br. s., 1H), 1.55 (s, 9H).

Workup

temperaturethe reaction mixture was cooled
extractionextracted into ethyl acetate
washwashed with water and brine
dry with materialthen dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was triturated with ether
additionwater, diluted with dichloromethane
customfinally the solvents removed in vacuo

Sources & evidence

ORD record: ord-29749230fc9e4587bbc5ac0079aff843
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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