1,1-Dichloroethane → HCID 59278198, compound

HRID 1698150Notes

Reaction equation

HRID 1698150 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([C@@H:11]([NH:15][C:16]([C:18]2[C:19]3[CH:26]=[N:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[C:20]=3[CH:21]=[N:22][CH:23]=2)=[O:17])[CH2:12][CH:13]=[O:14])[CH:8]=[CH:7][N:6]=1)(=[O:4])=[O:3].ClC(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC#N>[OH:14][CH2:13][CH2:12][C@H:11]([NH:15][C:16]([C:18]1[C:19]2[CH:26]=[N:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[C:20]=2[CH:21]=[N:22][CH:23]=1)=[O:17])[C:9]1[CH:8]=[CH:7][N:6]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:10]=1

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 59278338HCID 59278338, compound

Product 1

HCID 59278198HCID 59278198, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a room temperature solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-methanesulfonyl-pyridin-4-yl)-3-oxo-propyl]-amide (0.10 mg, 0.21 mmol) in a 9:1 mixture of dichloroethane in CH3CN (5 mL) was added sodium triacetoxyborohydride (181 mg, 0.854 mmol). After 36 hours, the reaction mixture was quenched with saturated aqueous sodium bicarbonate (10 mL) and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The oily residue was purified by silica gel chromatography using a gradient of 0-8% methanol in dichloromethane to afford the title compound as a white solid.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate (10 mL)
  2. extractionthe aqueous layer was extracted with dichloromethane (3×10 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe oily residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-803b73ec670e48d98bf120533d14f1a8
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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