Ammonia → HCID 66604278, compound

HRID 2410856Notes

Reaction equation

HRID 2410856 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]=[C:14]([N:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[CH:13]=[C:12]([C:22]([O:24]C)=O)[C:8]=3[NH:9][C:10]=2[CH:11]=1.[NH3:26]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]=[C:14]([N:16]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]4)[CH:13]=[C:12]([C:22]([NH2:26])=[O:24])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66605740HCID 66605740, compound

Product 1

HCID 66604278HCID 66604278, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of methyl 7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (15 mg, 0.044 mmol) and 7 N NH3 in MeOH (1.5 mL) in a sealed microwave tube was heated at 75° C. for 40 h. Removal of solvent to afford 7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (14 mg, 0.038 mmol, 87% yield) as a solid. MS (ESI) m/z 325.1 (M+H). 1H NMR (500 MHz, MeOD) δ ppm 8.04 (1H, d, J=8.85 Hz), 7.21 (1H, s), 7.06 (1H, d, J=2.14 Hz), 6.82 (1H, dd, J=8.70, 2.29 Hz), 3.91 (3H, s), 3.49-3.62 (4H, m), 1.74-1.82 (4H, m), 1.66-1.73 (2H, m).

Workup

  1. customRemoval of solvent

Sources & evidence

ORD record
ord-222efc7a67ad47ad8dc7f7258c1d3892
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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