Pyrrolidine → HCID 117770696, compound

HRID 1526357Notes

Reaction equation

HRID 1526357 reaction equation
[NH2:1][C:2]1[C:6]2[C:7](=[O:25])[N:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=O)[S:14][CH:15]=3)[C:5]=2[NH:4][N:3]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(#N)C>[NH2:1][C:2]1[C:6]2[C:7](=[O:25])[N:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH2:16][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[S:14][CH:15]=3)[C:5]=2[NH:4][N:3]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 1177707212-Thiophenecarboxaldehyde, 4-[3-amino-5-(2-chlorophenyl)-4,5-dihydro-4-oxo-1H-pyrazolo[4,3-c]pyridin-7-yl]-

Product 1

HCID 117770696HCID 117770696, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(3-amino-5-(2-chlorophenyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-7-yl)thiophene-2-carbaldehyde obtained in Step A (100 mg) and pyrrolidine (0.053 mL) in acetonitrile (10 mL) was added sodium triacetoxyborohydride (89 mg) at room temperature, and the mixture was stirred at room temperature 3 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, methanol/ethyl acetate) to give the title compound (63.1 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (basic silica gel, methanol/ethyl acetate)

Sources & evidence

ORD record
ord-d0c9f7d67f4f4108a8d76723c250f811
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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