Acetic Acid → HCID 57731586, compound

HRID 2234712Notes

Reaction equation

HRID 2234712 reaction equation
[CH3:1][N:2]([CH3:47])[C:3]([C:5]1[N:6](S(C2C=CC(C)=CC=2)(=O)=O)[N:7]=[C:8]([C:10]2[CH:11]=[C:12]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH3:26])=[CH:17][N:16](S(C4C=CC(C)=CC=4)(=O)=O)[C:13]3=[N:14][CH:15]=2)[CH:9]=1)=[O:4].CN(C)C=O.[OH-].[K+].C(O)(=O)C>CO.O>[CH3:1][N:2]([CH3:47])[C:3]([C:5]1[NH:6][N:7]=[C:8]([C:10]2[CH:11]=[C:12]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH3:26])=[CH:17][NH:16][C:13]3=[N:14][CH:15]=2)[CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 57731556HCID 57731556, compound

Product 1

HCID 57731586HCID 57731586, compoundYield 25.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-(toluene-4-sulfonyl)-2H-pyrazole-3-carboxylic acid dimethylamide (90 mg, 0.174 mmol) was dissolved in methanol (0.5 mL) and dimethylformamide (0.5 mL) and 50% w/v aqueous potassium hydroxide (0.5 mL) was added. After 3 hours, acetic acid (0.5 mL) was added and the mixture diluted with water. The solids were collected by filtration and the material purified by preparative HPLC to afford 5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2H-pyrazole-3-carboxylic acid dimethylamide (16.0 mg, 25.4%) 1H-NMR (500 MHz, dimethylsulfoxide-d6, 70° C.) δ 3.06-3.15 (s, 6H), 3.83 (s, 3H), 6.98 (br s, 1H), 7.07 (t, J=7.5 Hz, 1H), 7.14 (d, J=8.0 Hz, 1H), 7.31 (Br t, J=8.5 Hz, 1H), 7.60 (br d, J=6.0 Hz, 1H), 7.71 (Br s, 1H), 8.39 (br s, 1H), 8.67 (br s, 1H). MS: m/z 362 (M+H+).

Workup

  1. additionwas added
  2. filtrationThe solids were collected by filtration
  3. customthe material purified by preparative HPLC

Sources & evidence

ORD record
ord-f07ef6a5c8f24ec999e17512110cb500
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

Loading…