Sodium borohydride → (s)-5-(2,4-Difluorophenoxy)-1-isobutyl-1h-indazole-6-carboxylic acid {1-hydroxymethyl-3-[(2-methoxyethyl)-methylamino]-propyl}-amide

HRID 1897500Notes

Reaction equation

HRID 1897500 reaction equation
C[O:2][C:3](=O)[C@@H:4]([NH:13][C:14]([C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[N:21][N:22]2[CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:18][C:17]=1[O:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[F:37])=[O:15])[CH2:5][CH2:6][N:7]([CH2:9][CH2:10][O:11][CH3:12])[CH3:8].[BH4-].[Na+]>C1COCC1.CO>[OH:2][CH2:3][C@@H:4]([NH:13][C:14]([C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[N:21][N:22]2[CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:18][C:17]=1[O:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[F:37])=[O:15])[CH2:5][CH2:6][N:7]([CH2:9][CH2:10][O:11][CH3:12])[CH3:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67413409HCID 67413409, compound

Product 1

HCID 67410576(s)-5-(2,4-Difluorophenoxy)-1-isobutyl-1h-indazole-6-carboxylic acid {1-hydroxymethyl-3-[(2-methoxyethyl)-methylamino]-propyl}-amideYield 32.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

(S)-2-{[5-(2,4-Difluorophenoxy)-1-isobutyl-1H-indazole-6-carbonyl]-amino}-4-[(2-methoxyethyl)-methylamino]-butyric acid methyl ester (0.023 g, 0.043 mmol) and NaBH4 (0.016 g, 0.43 mmol) were dissolved in THF/MeOH (7 mL, 5:2) and heated to 70° C. in a sealed vial for 5 hours. The mixture was cooled to room temperature, concentrated under reduced pressure and chromatographed eluting with TEA/ethyl acetate (1:4) to provide 0.007 g of the product as viscous oil (31% yield). MS (APCI+) m/z 505 (M+1) detected.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customchromatographed
  4. washeluting with TEA/ethyl acetate (1:4)

Sources & evidence

ORD record
ord-73b9dad906dc4c49a81a4ae5f6b28f77
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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