Water → HCID 59278239, compound

HRID 2198183Notes

Reaction equation

HRID 2198183 reaction equation
[OH:1][C@H:2]([CH2:34][OH:35])[CH2:3][C@H:4]([NH:15][C:16]([C:18]1[C:19]2[CH:26]=[N:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:20]=2[CH:21]=[N:22][CH:23]=1)=[O:17])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:6]=1.C1N=CN([C:41](N2C=NC=C2)=[O:42])C=1.O>CN(C=O)C>[CH3:14][S:11]([C:7]1[CH:6]=[C:5]([C@@H:4]([NH:15][C:16]([C:18]2[C:19]3[CH:26]=[N:25][N:24]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[C:20]=3[CH:21]=[N:22][CH:23]=2)=[O:17])[CH2:3][CH:2]2[CH2:34][O:35][C:41](=[O:42])[O:1]2)[CH:10]=[CH:9][N:8]=1)(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 59278138HCID 59278138, compound

Product 1

HCID 59278239HCID 59278239, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a chilled (0° C.) solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(1S,3S)-3,4-dihydroxy-1-(2-methanesulfonyl-pyridin-4-yl)-butyl]-amide (50.0 mg, 0.100 mmol) in DMF (1 mL) was added CDI (32.4 mg, 0.200 mmol). The mixture was then allowed to warm to room temperature. After 12 hours, the reaction was poured in to water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with aqueous ammonium chloride (3×10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-6% methanol in methylene chloride. The solid from the column chromatography was crystallized from methylene chloride to afford the title compound as white needle-shaped crystals. MS m/z 526.64 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layers were washed with aqueous ammonium chloride (3×10 mL) and brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a gradient of 0-6% methanol in methylene chloride
  8. customThe solid from the column chromatography was crystallized from methylene chloride

Sources & evidence

ORD record
ord-5285816b9b3c4b6ca55bd601d34c0193
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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