Ammonium Hydroxide → 2-amino-9-benzyl-9H-pyrido[2,3-b]indole-3-carboxamide

HRID 1158729Notes

Reaction equation

HRID 1158729 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](/[CH:17]=[C:18](\[C:22]#[N:23])/[C:19]([NH2:21])=[O:20])=[C:9]1OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:27].[OH-]>CO>[NH2:23][C:22]1[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:9]=2[N:27]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 59513624(2E)-3-(1-benzyl-2-ethoxy-1H-indol-3-yl)-2-cyanoacrylamide

Product 1

HCID 595136372-amino-9-benzyl-9H-pyrido[2,3-b]indole-3-carboxamideYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2E)-3-(1-benzyl-2-ethoxy-1H-indol-3-yl)-2-cyanoacrylamide (vi-a, 2.00 g, 5.79 mmol) in MeOH (150 mL) was added NH4OH (30% weight solution of NH3 in water, 100 mL). The reaction was stirred at RT overnight. The reaction was concentrated under reduced pressure and the crude solid was triturated with H2O. The solid was filtered and triturated again with ether. A yellow solid was collected by suction filtration to yield 2-amino-9-benzyl-9H-pyrido[2,3-b]indole-3-carboxamide (vii-a, 1.23 g, 63%). NH4OAc standard conditions. DAD Retention time =7.25 min. M+H=317. 1H NMR (300 MHz, DMSO-d6): δ 8.77 (s, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.62 (br s, 2H), 7.40 (d, J=7.7 Hz, 1H), 7.31-7.16 (m, 9H), 5.52 (s, 2H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe crude solid was triturated with H2O
  3. filtrationThe solid was filtered
  4. customtriturated again with ether
  5. filtrationA yellow solid was collected by suction filtration

Sources & evidence

ORD record
ord-039e36d05910438d9934179e435f14b4
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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