Ammonia → 7-(morpholinosulfonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide

HRID 2410869Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[C:14]4[N:22]=[C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH:20]=[C:19]([C:29]([O:31]C)=O)[C:15]=4[NH:16][C:17]=3[CH:18]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1.[NH3:33]>CO>[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[C:14]4[N:22]=[C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH:20]=[C:19]([C:29]([NH2:33])=[O:31])[C:15]=4[NH:16][C:17]=3[CH:18]=2)(=[O:8])=[O:9])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of methyl 7-(morpholinosulfonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (106 mg, 0.235 mmol) in 7 N NH3 in MeOH (5 mL) in a sealed microwave vial was heated at 80° C. overnight. After cooling to RT, the precipitate was collected, washed with MeOH, and dried to leave 7-(morpholinosulfonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide (67 mg, 0.15 mmol, 62% yield) as yellow fluffy solid. MS (ESI) m/z 435.1 (M−H). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.03 (1H, s), 8.70 (1H, s), 8.59 (1H, s), 8.52 (1H, d, J=8.06 Hz), 8.33 (2H, d, J=7.30 Hz), 8.21 (1H, d, J=1.01 Hz), 8.00 (1H, s), 7.52-7.64 (3H, m), 7.46 (1H, t, J=7.30 Hz), 3.60-3.69 (4H, m), 2.88-2.97 (4H, m).

Workup

temperatureAfter cooling to RT
customthe precipitate was collected
washwashed with MeOH
customdried

Sources & evidence

ORD record: ord-f8604a63d76d4810ba6467ae7071a3ff
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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