Sodium borohydride → HCID 178515761, compound

HRID 1890292Notes

Reaction equation

HRID 1890292 reaction equation
[OH:1][C:2]1[N:7]=[C:6]2[N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3=[O:17])[CH:9]=[N:10][C:5]2=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[OH:17][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[N:8]1[C:6]2=[N:7][C:2]([OH:1])=[CH:3][CH:4]=[C:5]2[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178515950HCID 178515950, compound

Product 1

HCID 178515761HCID 178515761, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(5-Hydroxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclohexanone (0.200 g, 0.865 mmol) was taken up in ethanol (4 mL) and sodium borohydride (9.8 mg, 0.26 mmol) added. The reaction was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was purified by preparative HPLC to give the title compound (0.135 g). LCMS m/z=234.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35-1.60 (m, 4H), 1.75-1.95 (m, 2H), 2.00-2.15 (m, 2H), 4.00-4.10 (m, 1H), 4.38 (q, J=8.1 Hz, 1H), 6.92 (d, J=8.8 Hz, 1H), 8.18 (d, J=8.8 Hz, 1H), 9.52 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f96e07bb732943948c038a098cbd7a91
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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