Sodium borohydride → HCID 67410837, compound

HRID 1897494Notes

Reaction equation

HRID 1897494 reaction equation
[BH4-].[Na+].C[O:4][C:5](=O)[C@@H:6]([NH:15][C:16]([C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[N:23][N:24]2[CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:20][C:19]=1[O:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[F:39])=[O:17])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>CO>[OH:4][CH2:5][C@@H:6]([NH:15][C:16]([C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[N:23][N:24]2[CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:20][C:19]=1[O:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[F:39])=[O:17])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67410827HCID 67410827, compound

Product 1

HCID 67410837HCID 67410837, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Sodium borohydride (0.012 g, 0.31 mmol) was added portion-wise to a heated (50° C.) solution of (S)-2-{[5-(2,4-difluoro-phenoxy)-1-isobutyl-1H-indazole-6-carbonyl]-amino}-4-piperidin-1-yl-butyric acid methyl ester (0.022 g, 0.042 mmol) in MeOH. The reaction mixture was stirred at 50° C. until HPLC analysis showed consumption of the starting material. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with ethyl acetate and 1N HCl. The organics were extracted with 1N HCl until the organic layer contained no product by HPLC analysis. The aqueous solution was basified to pH 14 with NaOH and then extracted with dichloromethane several times. The combined organics were dried over MgSO4 and concentrated under reduced pressure to afford 9.1 mg of oil (44% yield). MS (APCI+) m/z 501 (M+1) detected.

Workup

  1. customconsumption of the starting material
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate and 1N HCl
  5. extractionThe organics were extracted with 1N HCl until the organic layer
  6. extractionextracted with dichloromethane several times
  7. dry with materialThe combined organics were dried over MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ba0cfe77f564018a90e8cc3be6a9240
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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