HCID 66606459, compound → HCID 66604922, compound

HRID 2410818Notes

Reaction equation

HRID 2410818 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:16]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:14]=[C:13]([C:27]([NH2:29])=[O:28])[C:9]=3[NH:10][C:11]=2[CH:12]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:16]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:14]=[C:13]([C:27]([NH2:29])=[O:28])[C:9]=3[NH:10][C:11]=2[CH:12]=1

Participants

4

Reactant 1

HCID 66606459HCID 66606459, compound

Product 1

HCID 66604922HCID 66604922, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-nitro-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (200 mg, 0.500 mmol) and Pd-C (200 mg, 0.188 mmol)in MeOH (5 mL) under a H2 balloon was stirred for 3 hr. Filtration followed by preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, 10-60% B at 42 mL/min over 20 min) and SCX capture and release with 2 N NH3 in MeOH afforded 7-amino-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (80 mg, 0.21 mmol, 41% yield). MS (ESI) m/z 371.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.16 (1H, d, J=4.58 Hz), 8.58 (2H, br. s.), 8.51 (1H, br. s.), 8.25-8.37 (1H, m), 7.86-7.99 (1H, m), 7.75 (3H, d, J=6.10 Hz), 6.82 (1H, d, J=3.36 Hz), 6.48-6.67 (1H, m), 5.61 (2H, br. s.).

Workup

  1. filtrationFiltration
  2. customfollowed by preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, 10-60% B at 42 mL/min over 20 min) and SCX capture and release with 2 N NH3 in MeOH

Sources & evidence

ORD record
ord-46ba383864bc4b9b8624c87671ae1058
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…