Water → HCID 117652419, compound

HRID 1500831Notes

Reaction equation

HRID 1500831 reaction equation
[CH3:1][N:2]([CH3:44])[CH2:3]/[CH:4]=[CH:5]/[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:16]=[C:17]3[C:23]([C:24]4[CH:29]=[C:28]([CH3:30])[C:27]([F:31])=[CH:26][C:25]=4[O:32][CH3:33])=[CH:22][N:21](S(C4C=CC(C)=CC=4)(=O)=O)[C:18]3=[N:19][CH:20]=2)[CH:10]=1)=[O:7].O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:44][N:2]([CH3:1])[CH2:3]/[CH:4]=[CH:5]/[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:16]=[C:17]3[C:23]([C:24]4[CH:29]=[C:28]([CH3:30])[C:27]([F:31])=[CH:26][C:25]=4[O:32][CH3:33])=[CH:22][NH:21][C:18]3=[N:19][CH:20]=2)[CH:10]=1)=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 117652600HCID 117652600, compound

Product 1

HCID 117652419HCID 117652419, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (E)-4-(dimethylamino)-N-(3-(3-(4-fluoro-2-methoxy-5-methylphenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)but-2-enamide 137 (60 mg, 0.098 mmol) was taken in methanol (7 mL) and water (3 mL) was added potassium carbonate (54.10 mg, 0.392 mmol). The reaction was heated to 60° C. for overnight. The methanol was completely distilled and diluted with water. The organic phase was extracted with ethyl acetate (50 mL) twice. The organic layer was dried over sodium sulphate and filtered and concentrated to get the crude. The crude was purified through flash chromatography by using neutral alumina. The compound was eluted in 2% methanol in chloroform as half white solid (E)-4-(dimethylamino)-N-(3-(3-(4-fluoro-2-methoxy-5-methylphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)but-2-enamide 138. MS-ES+458.3, 1H NMR (400 MHz, DMSO): 11.89 (s, 1H), 10.14 (s, 1H), 8.48 (d, 1H), 8.05 (d, 2H), 7.63 (m, 2H), 7.40 (m, 3H), 6.98 (d, 1H), 6.73 (m, 1H), 6.26 (d, 1H), 3.80 (s, 3H), 3.06 (s, 3H), 2.23 (d, 3H), 2.18 (s, 6H).

Workup

  1. distillationThe methanol was completely distilled
  2. additiondiluted with water
  3. extractionThe organic phase was extracted with ethyl acetate (50 mL) twice
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto get the crude
  8. customThe crude was purified through flash chromatography
  9. washThe compound was eluted in 2% methanol in chloroform as half white solid (E)-4-(dimethylamino)-N-(3-(3-(4-fluoro-2-methoxy-5-methylphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)but-2-enamide 138

Sources & evidence

ORD record
ord-63902e1214dc47f796065967e1d15ecd
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

Loading…