Sodium borohydride → HCID 67412477, compound

HRID 1897486Notes

Reaction equation

HRID 1897486 reaction equation
[CH3:1][O:2][C:3]1[CH:45]=[CH:44][C:6]([CH2:7][N:8]([CH:41]([CH3:43])[CH3:42])[CH2:9][CH2:10][C@H:11]([NH:16][C:17]([C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[N:24][N:25]3[CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:21][C:20]=2[O:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=2[F:40])=[O:18])[C:12](OC)=[O:13])=[CH:5][CH:4]=1.[BH4-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:45]=[CH:44][C:6]([CH2:7][N:8]([CH:41]([CH3:43])[CH3:42])[CH2:9][CH2:10][C@H:11]([NH:16][C:17]([C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[N:24][N:25]3[CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:21][C:20]=2[O:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=2[F:40])=[O:18])[CH2:12][OH:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67413214HCID 67413214, compound

Product 1

HCID 67412477HCID 67412477, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(S)-methyl 4-((4-methoxybenzyl)(isopropyl)amino)-2-(5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole-6-carboxamido)butanoate (0.035 g, 0.057 mmol) and NaBH4 (0.022 g, 0.57 mmol) were dissolved in THF/MeOH (5 mL, 3:2) and heated to 50° C. for 3 hours. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was chromatographed eluting with 5% MeOH in dichloromethane with 1% triethylamine to provide 0.020 g of gel (59% yield).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was chromatographed
  4. washeluting with 5% MeOH in dichloromethane with 1% triethylamine

Sources & evidence

ORD record
ord-ad1d574939ca4654b5ec2c808a5ac70c
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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