Methanesulfonyl chloride → HCID 86640801, compound

HRID 1698153Notes

Reaction equation

HRID 1698153 reaction equation
[OH:1][CH2:2][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.C(N(CC)C(C)C)(C)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>ClCCl>[F:33][C:30]1[CH:29]=[CH:28][C:27]([N:24]2[C:20]3[CH:21]=[N:22][CH:23]=[C:18]([C:16]([NH:15][C@H:4]([C:5]4[CH:10]=[CH:9][N:8]=[C:7]([S:11]([CH3:14])(=[O:12])=[O:13])[CH:6]=4)[CH2:3][CH2:2][O:1][S:44]([CH3:43])(=[O:46])=[O:45])=[O:17])[C:19]=3[CH:26]=[N:25]2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59278198HCID 59278198, compound

Product 1

HCID 86640801HCID 86640801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-3-hydroxy-1-(2-methanesulfonyl-pyridin-4-yl)-propyl]-amide (0.10 g, 0.21 mmol) and N,N-diisopropylethylamine (167 μL, 0.957 mmol) in dichloromethane (20 mL) was cooled in an ice water-brine bath. After 5 minutes, methanesulfonyl chloride (25 μL, 0.32 mmol) was added and the cold bath was removed until the mixture became homogeneous. The mixture was again cooled in an ice bath. After 30 minutes, the mixture was quenched with saturated aqueous ammonium chloride (10 mL), washed with brine (10 mL), dried over magnesium sulfate and concentrated to afford methanesulfonic acid (S)-3-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-3-(2-methanesulfonyl-pyridin-4-yl)-propyl ester which was used without further purification.

Workup

  1. customthe cold bath was removed until the mixture
  2. temperatureThe mixture was again cooled in an ice bath
  3. waitAfter 30 minutes
  4. customthe mixture was quenched with saturated aqueous ammonium chloride (10 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6fc5f5c5585d416eb9cda8517cf41b96
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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