Ammonia → HCID 86663052, compound

HRID 2410809Notes

Reaction equation

HRID 2410809 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:22]([O:24]C)=O)[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([N:15]4[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]4)[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.[NH3:26]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:22]([NH2:26])=[O:24])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([N:15]4[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]4)[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86663050HCID 86663050, compound

Product 1

HCID 86663052HCID 86663052, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-bromo-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (300 mg, 0.744 mmol) and 7 N NH3 in MeOH (5 mL) in a sealed microwave vial was heated in an oil bath at 80° C. for 16 h. After cooling to RT, the solid was collected by filtration, washed with MeOH, and air-dried to afford 2-bromo-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (200 mg, 0.489 mmol, 66% yield). MS (ESI) m/z 390.0 (M+H); LCMS Ret Time: 1.242 min; PHENOMENEX® Luna S10 4.6×50 mm column, 3 min gradient, 0-100% B, 5 mL/min. Solvent A: 10% MeOH—90% H2O—0.1% TFA; Solvent B: 90% MeOH—10% H2O—0.1% TFA.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe solid was collected by filtration
  3. washwashed with MeOH
  4. customair-dried

Sources & evidence

ORD record
ord-ae2d968e94634b7799b37bf7ec6facdd
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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