Methanol → HCID 59593315, compound

HRID 2261568Notes

Reaction equation

HRID 2261568 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([CH:19]([C:21]3[CH:22]=[N:23][C:24]([CH2:27][NH:28][C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)=[CH:25][CH:26]=3)[OH:20])=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[K+].O.[CH3:39]O>>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([CH:19]([O:20][CH3:39])[C:12]3[C:13]4[C:14](=[N:15][CH:16]=[CH:17][CH:18]=4)[NH:10][CH:11]=3)=[CH:22][N:23]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 14797Potassium HydroxideHCID 59593298HCID 59593298, compound

Product 1

HCID 59593315HCID 59593315, compound

Conditions

Temperature
50 °C

Procedure

To (1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-[(4-chloro-phenylamino)-methyl]-pyridin-3-yl-methanol (56, 120.0 mg, 0.24 mmol) in methanol (20.0 mL) were added potassium hydroxide (0.400 g, 7.13 mmol) and water (5.0 mL, 0.28 mol). The reaction was heated to 50° C. for 10 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give compound (57, 30 mg, 33.0%). MS (ESI) [M+H+]+=379.4.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane
  7. customto give compound (57, 30 mg, 33.0%)

Sources & evidence

ORD record
ord-62dd84d3110041a5a13b003cfc593193
Source dataset
uspto-grants-2010_12
Patent number
US07846941B2

Reaction notes

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