Sodium borohydride → HCID 25073835, compound

HRID 1966818Notes

Reaction equation

HRID 1966818 reaction equation
[BH4-].[Na+].[CH:3]1([NH:9][C:10]2[C:15]([C:16]3[CH2:20][C:19]([CH2:25][C:26](OC)=[O:27])([C:21](OC)=[O:22])[O:18][N:17]=3)=[CH:14][N:13]=[C:12]3[N:30]([CH2:33][CH3:34])[N:31]=[CH:32][C:11]=23)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>O1CCCC1.CO>[CH:3]1([NH:9][C:10]2[C:15]([C:16]3[CH2:20][C:19]([CH2:25][CH2:26][OH:27])([CH2:21][OH:22])[O:18][N:17]=3)=[CH:14][N:13]=[C:12]3[N:30]([CH2:33][CH3:34])[N:31]=[CH:32][C:11]=23)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66733157HCID 66733157, compound

Product 1

HCID 25073835HCID 25073835, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (14 mg, 0.00036 mole) was added to methyl 3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-5-(2-methoxy-2-oxoethyl)-4,5-dihydroisoxazole-5-carboxylate (80 mg, 0.00018 mole) (example 10) in tetrahydrofuran (5 ml). Methanol (2 drops) was added and the reaction mixture was stirred at room temperature overnight. It was quenched with saturated ammonium chloride solution, diluted with ethyl acetate and extracted with brine. The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was purified by column chromatography.

Workup

  1. customIt was quenched with saturated ammonium chloride solution
  2. additiondiluted with ethyl acetate
  3. extractionextracted with brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-7ce56d18ecd24a0ca6f9ea9d4388cb35
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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