Ammonia → 8-chloro-7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide

HRID 2410732Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of methyl 8-chloro-7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (29 mg, 0.073 mmol) in a 7 N solution of ammonia in MeOH (7 mL) in a sealed microwave vial was heated at 80° C. for 24 hr. The solvents were removed and preparative HPLC (100×30 mm Luna C18 column, gradient elution with A:B=30:70 to A:B=0:100 [A=10 mM NH4OAc in 5% aqueous CH3CN; B=10 mM NH4OAc in 95% aqueous CH3CN] over 20 min) afforded 8-chloro-7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (16 mg) as a yellow solid. MS (ESI) m/z 380.1 (M+H). 1H NMR (MeOD) δ ppm 8.36 (1H, s), 8.13 (1H, s), 8.06 (2H, d, J=8.85 Hz), 7.31 (1H, s), 7.10 (2H, d, J=8.85 Hz), 4.03 (3H, s), 3.90 (3H, s).

Workup

customThe solvents were removed
washpreparative HPLC (100×30 mm Luna C18 column, gradient elution with A:B=30:70 to A:B=0:100 [A=10 mM NH4OAc in 5% aqueous CH3CN

Sources & evidence

ORD record: ord-0a74062825fe4bcd8e72acbfc960952e
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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