Ammonia → HCID 136340637, compound

HRID 2410812Notes

Reaction equation

HRID 2410812 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:29]([O:31]C)=O)[C:12]3[NH:13][C:14]4[CH:15]=[C:16]([N:22]5[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]5)[CH:17]=[CH:18][C:19]=4[C:20]=3[N:21]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[NH3:33]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:29]([NH2:33])=[O:31])[C:12]3[NH:13][C:14]4[CH:15]=[C:16]([N:22]5[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]5)[CH:17]=[CH:18][C:19]=4[C:20]=3[N:21]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 136337375HCID 136337375, compound

Product 1

HCID 136340637HCID 136340637, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-(3-chloro-4-hydroxyphenyl)-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (100 mg, 0.222 mmol) and 7N NH3 in MeOH (5 mL) in a sealed microwave vessel was heated in an oil bath at 80° C. for 16 h. After cooling to RT, the solid was collected by filtration, and washed with MeOH, and air-dried to afford 2-(3-chloro-4-hydroxyphenyl)-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (75 mg, 0.16 mmol, 74% yield). MS (ESI) m/z 436.10 (M+H).

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-4815027beb1643ff961a1200e4a8dd88
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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