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

HRID 2410724Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[CH:16]=[C:15]([C:27]([O:29]C)=O)[C:11]=3[NH:12][C:13]=2[CH:14]=1.[NH3:31]>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:18]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=4)[CH:16]=[C:15]([C:27]([NH2:31])=[O:29])[C:11]=3[NH:12][C:13]=2[CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of methyl 7-(2-methoxyethoxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (28 mg, 0.069 mmol) in 7 N ammonia in MeOH (3mL) in a sealed microwave vial was heated at 60° C. for 22 hr. The solvent was removed and the residue was purified by radial chromatography (step gradient elution with DCM containing 2 to 4% MeOH) to give 7-(2-methoxyethoxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (20 mg). MS (ESI) m/z 392.1 (M+H). 1H NMR (MeOD) δ ppm 8.26 (1H, d, J=8.55 Hz), 8.07 (1H, s), 8.01-8.06 (2H, m), 7.16 (1H, d, J=2.14 Hz), 7.06-7.11 (2H, m), 6.94 (1H, d, J=8.55 Hz), 4.21-4.29(2H, m), 3.89(3H, s), 3.83 (2H, dd), 3.45-3.51 (3H, s).

Workup

customThe solvent was removed
customthe residue was purified by radial chromatography (step gradient elution with DCM containing 2 to 4% MeOH)

Sources & evidence

ORD record: ord-89ecad7f56d7474c9916b3fa9f3463ff
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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