Sodium borohydride → HCID 71280581, compound

HRID 1497938Notes

Reaction equation

HRID 1497938 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:16][C:15]4([CH2:19][C:18](=[O:20])[CH2:17]4)[CH2:14]3)[O:10][N:9]=2)=[CH:4][C:3]=1[NH:21][C:22]([C:24]1[N:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]2=[N:26][CH:25]=1)=[O:23].[BH4-].[Na+]>CO>[OH:20][CH:18]1[CH2:19][C:15]2([CH2:14][CH:13]([C:11]3[O:10][N:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:21][C:22]([C:24]5[N:28]6[CH:29]=[CH:30][CH:31]=[CH:32][C:27]6=[N:26][CH:25]=5)=[O:23])[CH:4]=4)[N:12]=3)[CH2:16]2)[CH2:17]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71280624HCID 71280624, compound

Product 1

HCID 71280581HCID 71280581, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of N-(2-methyl-5-(5-(6-oxospiro[3.3]heptan-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (F76) (100 mg, 0.23 mmol) in anhydrous methanol (1 mL) was added sodium borohydride (10.6 mg, 0.28 mmol). The reaction mixture was stirred at room temperature for 12 hours. The reaction was quenched with water and the solvent was concentrated. Purification by silica gel using 10% MeOH in dichloromethane afforded N-(5-(5-(6-hydroxyspiro[3.3]heptan-2-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F100). MS m/z 430.1 (M+1)+.

Workup

  1. customThe reaction was quenched with water
  2. concentrationthe solvent was concentrated
  3. customPurification by silica gel using 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-a769035ebfa9456c98cb7afc0a536eac
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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