Water → HCID 117652627, compound

HRID 1500834Notes

Reaction equation

HRID 1500834 reaction equation
[F:1][C:2]1[C:3]([O:46][CH3:47])=[C:4]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[C:20](/[CH:25]=[C:26](\[CH3:35])/[C:27]([NH:29][C:30]([CH3:34])([CH3:33])[CH2:31][OH:32])=[O:28])[CH:21]=[CH:22][C:23]=4[F:24])[CH:16]=3)[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.O.C(=O)([O-])[O-].[K+].[K+]>CO>[F:1][C:2]1[C:3]([O:46][CH3:47])=[C:4]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[C:20](/[CH:25]=[C:26](\[CH3:35])/[C:27]([NH:29][C:30]([CH3:33])([CH3:34])[CH2:31][OH:32])=[O:28])[CH:21]=[CH:22][C:23]=4[F:24])[CH:16]=3)[NH:11][CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 117652547HCID 117652547, compound

Product 1

HCID 117652627HCID 117652627, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 163 (40 mg) was taken in methanol (7 mL) and water (3 mL) was added potassium carbonate (20 mg). 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 triturated with hexane to afford the half white colour solid (E)-3-(3-(3-(3,5-difluoro-2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-4-fluorophenyl)-N-(1-hydroxy-2-methylpropan-2-yl)-2-methylacrylamide 164. MS-ES+486.19, 1H NMR (400 MHz, CDCl3): 9.6 (s, 1H), 8.31 (s, 1H), 8.05 (s, 1H), 7.52 (s, 1H) 7.44 (s, 3H), 7.22 (m, 1H), 7.1 (d, 1H), 6.8(m, 1H), 5.91 (s, 1H), 3.74 (s, 3H), 2.116 (s, 3H), 1.41 (s, 9H).

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 triturated with hexane

Sources & evidence

ORD record
ord-4de0cbd8a1ce458bb34108b335e94217
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

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