Sodium borohydride → HCID 11710266, compound

HRID 1821647Notes

Reaction equation

HRID 1821647 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH:24]=3)[CH:22]=[O:23])[N:15]=2)[NH:10][C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[C:16]2=[N:15][C:14]([C:17]3[CH:18]=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH2:22][OH:23])[CH:24]=3)=[CH:13][N:12]=[C:11]2[NH:10][C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11653391HCID 11653391, compound

Product 1

HCID 11710266HCID 11710266, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(3-Benzyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)-2-methoxybenzaldehyde (27.2 mg, 0.076 mmol) in MeOH (1 mL) was added NaBH4 (2.86 mg, 0.076 mmol). The mixture was stirred at room temperature for one hour, and then concentrated under reduced pressure. The residue thus obtained was purified by column chromatography [silica gel; MeOH/DCM (1:19)] to give the product as an off-white powder (22 mg, 80%). 1H NMR (400 MHz, DMSO): δ 8.35 (s, 1H), 8.01 (s, 1H), 7.84 (dd, J=2.0, 8.8 Hz, 1H), 7.40-7.25 (m, 5H), 7.02 (d, J=8.4 Hz, 1H), 5.04 (s, 2H), 4.52 (d, J=5.2 Hz, 2H), 3.81 (s, 3H). MS: 363.0 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by column chromatography [silica gel; MeOH/DCM (1:19)]

Sources & evidence

ORD record
ord-bd7531c1ed78407fb84e6d85e9b29c11
Source dataset
uspto-grants-2009_10
Patent number
US07608622B2

Reaction notes

Loading…