Water → HCID 57963226, compound

HRID 1692834Notes

Reaction equation

HRID 1692834 reaction equation
C1(S([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([O:19][CH3:20])[C:13]=3[C:12]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[Cl:37])=[N:26][C:27]=3[F:28])=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[K+].O>CO>[Cl:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][NH:29][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C:12]2[C:13]3[C:18]([O:19][CH3:20])=[N:17][CH:16]=[N:15][C:14]=3[NH:10][CH:11]=2)=[C:27]([F:28])[N:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 57963186HCID 57963186, compound

Product 1

HCID 57963226HCID 57963226, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To [5-(7-benzenesulfonyl-4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-6-fluoro-pyridin-2-yl]-(2-chloro-benzyl)-amine (45, 0.30 g, 0.558 mmol) in 15 mL of methanol, potassium hydroxide (0.50 g, 8.9 mmol) was added. The reaction was stirred at 45° C. for 2 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was washed with ethyl acetate to provide the desired compound (P-0090, 0.176 g). MS (ESI) [M+H+]+=397.9.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. washThe resulting material was washed with ethyl acetate

Sources & evidence

ORD record
ord-d63d7dee952f4d2097f0200bb69a3f94
Source dataset
uspto-grants-2012_04
Patent number
US08158636B2

Reaction notes

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