Sodium borohydride → HCID 11574079, compound

HRID 1765342Notes

Reaction equation

HRID 1765342 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[NH:8][N:7]=[C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[N:12]([CH2:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:11]=2)[CH:5]=1>O1CCCC1>[OH:29][CH:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:21][N:12]1[N:11]=[C:10]([NH:9][C:6]2[CH:5]=[C:4]([CH3:3])[NH:8][N:7]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:20]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21106492HCID 21106492, compound

Product 1

HCID 11574079HCID 11574079, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (6 mg, 0.15 mmol) was added in one portion to a stirred solution of 4-(5-Methyl-1H-pyrazol-3-ylamino)-2-(2-oxo-2-phenyl-ethyl)-2H-phthalazin-1-one (17 mg, 0.05 mmol) (Example E-9) in tetrahydrofuran (THF) (1 ml). The reaction mixture was stirred at room temperature for two hours. After this time LC-MS indicated complete consumption of starting material, methanol (0.5 ml) was added and the reaction mixture was concentrated under vacuum. The resulting residue was purified by flash column chromatography (elution: 97% dichloromethane (DCM), 3% methanol (MeOH)) to give the title compound (2.2 mg, 12% yield) as a white solid. MS (ESI+)=(M+H)+ 361.98.

Workup

  1. customconsumption of starting material, methanol (0.5 ml)
  2. additionwas added
  3. concentrationthe reaction mixture was concentrated under vacuum
  4. customThe resulting residue was purified by flash column chromatography (elution: 97% dichloromethane (DCM), 3% methanol (MeOH))

Sources & evidence

ORD record
ord-eef59fbcdc454652822cd42ec936d253
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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