Sodium borohydride → HCID 25207402, compound

HRID 220226Notes

Reaction equation

HRID 220226 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[N:28]([CH2:32][CH2:33][OH:34])[N:27]=[CH:26]3)=[O:12])[N:7]([C:35]2[CH:40]=[CH:39][C:38]([CH:41]=[O:42])=[CH:37][CH:36]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[N:28]([CH2:32][CH2:33][OH:34])[N:27]=[CH:26]3)=[O:12])[N:7]([C:35]2[CH:36]=[CH:37][C:38]([CH2:41][OH:42])=[CH:39][CH:40]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86649456HCID 86649456, compound

Product 1

HCID 25207402HCID 25207402, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3-tert-butyl-1-(4-formylphenyl)-1H-pyrazol-5-yl)-3-((5-fluoro-2-(1-(2-hydroxyethyl)-1H-indazol-5-yloxy)phenyl)methyl)urea was treated with NaBH4 in MeOH and stirred at ambient temperature for 2 hours. The reaction was quenched with 2 N HCl, then neutralized with Na2CO3 and extracted into DCM. The organic layer was dried and concentrated, and the residue purified on a pyridine column eluting with 20% ethanol in hexanes to provide 1.3 mg (6.3%) of the desired material. MS M+1 (573).

Workup

  1. customThe reaction was quenched with 2 N HCl
  2. extractionextracted into DCM
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customthe residue purified on a pyridine column
  6. washeluting with 20% ethanol in hexanes

Sources & evidence

ORD record
ord-4520ab90aa3948809d92107f47d6a39e
Source dataset
uspto-grants-2012_06
Patent number
US08202899B2

Reaction notes

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