Sodium borohydride → HCID 11574079, compound

HRID 1783655Notes

Reaction equation

HRID 1783655 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>C1COCC1>[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 THF (1 ml). The reaction mixture was stirred at RT for two hours. After this time LC-MS indicated complete consumption of starting material, MeOH (0.5 ml) was added and the reaction mixture was concentrated under vacuum. The resulting residue was purified by flash column chromatography (elution: 97% DCM, 3% 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, MeOH (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% DCM, 3% MeOH)

Sources & evidence

ORD record
ord-c6f143917e1e44e6a87f700fe28f140d
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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