Hydrogen Peroxide → 4-amino-3-(3-methoxy-4-(1-methyl-1H-indole-2-carboxamido)phenyl)thieno[3,2-c]pyridine-7-carboxamide

HRID 1270936Notes

Reaction equation

HRID 1270936 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:32]#[N:33])=[CH:4][N:3]=1.C(=O)([O-])[O-:35].[K+].[K+].OO>CS(C)=O>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:32]([NH2:33])=[O:35])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 18450893N-[4-(4-amino-7-cyanothieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-indole-2-carboxamide

Product 1

HCID 184508294-amino-3-(3-methoxy-4-(1-methyl-1H-indole-2-carboxamido)phenyl)thieno[3,2-c]pyridine-7-carboxamideYield 4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N2-[4-(4-amino-7-cyanothieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-2-indolecarboxamide (A-825289.0, 50 mg, 0.11 mmol), potassium carbonate (61 mg, 0.44 mmol), and hydrogen peroxide (0.150 mL, 30% aqueous) were heated in dimethylsulfoxide (1 mL) for 25 minutes at 150° C. in a microwave. The mixture was evaporated, diluted in dimethylformamide, filtered, and the filtrate was purified by RP-HPLC to yield the title compound (2 mg, 4% yield): 1H NMR (DMSO-d6, 400 MHz) δ 9.50 (s, 1H), 8.57 (s, 1H), 8.00 (d, 1H), 7.71 (d, 1H), 7.58–7.62 (m, H), 7.06–7.35 (m, 5H), 4.04 (s, 3H); RP-HPLC (Conditions i) Rt 11.7 min. MS: 470.0 MH−.

Workup

  1. customThe mixture was evaporated
  2. additiondiluted in dimethylformamide
  3. filtrationfiltered
  4. customthe filtrate was purified by RP-HPLC

Sources & evidence

ORD record
ord-43999ecf996149989ef1873b2f919355
Source dataset
uspto-grants-2007_04
Patent number
US07202363B2

Reaction notes

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