Dimethylformamide → HCID 57731458, compound

HRID 2234707Notes

Reaction equation

HRID 2234707 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[N:23]=[C:22]([CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:21]=[N:20][CH:19]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.CN(C)C=O.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[N:23]=[C:22]([CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:21]=[N:20][CH:19]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 59297027HCID 59297027, compound

Product 1

HCID 57731458HCID 57731458, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{6-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrazin-2-yl}-N,N-dimethyl-acetamide (56.6 mg, 0.104 mmol) was dissolved in methanol (0.5 mL) and dimethylformamide (0.5 mL) and 50% w/v aqueous potassium hydroxide (0.2 mL) was added. After 5 hours, the reaction was quenched by addition of acetic acid (0.2 mL). The mixture was carefully poured into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and dried to a residue which was purified by preparative HPLC to afford 2-{6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrazin-2-yl}-N,N-dimethyl-acetamide (5.7 mg, 14.1%). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 2.74 (s, 3H), 2.90 (s, 3H), 3.78 (s, 3H), 3.96 (s, 2H), 7.01 (dt, J=1, J=7.5 Hz, 1H), 7.11 (br d, J=8 Hz, 1H), 7.28 (dt, J=1.5, J=8.5 Hz, 1H), 7.50 (dd, J=1.5 Hz, J=7.5 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 8.21 (d, J=2.5 Hz, 1H), 8.46 (d, J=2.0 Hz, 1H), 8.56 (d, J=2.5 Hz, 1H), 8.62 (d, J=2.5 Hz, 1H). MS: m/z 388 (M+H+).

Workup

  1. additionwas added
  2. customthe reaction was quenched by addition of acetic acid (0.2 mL)
  3. additionThe mixture was carefully poured into saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried to a residue which
  8. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-095f33c2be7e44c2825f02b24bc19151
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

Loading…