Sodium borohydride → HCID 70874001, compound

HRID 2208933Notes

Reaction equation

HRID 2208933 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:22]([CH2:30][CH3:31])[CH:23]2[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:22]([CH2:30][CH3:31])[CH:23]2[CH2:24][CH2:25][CH:26]([OH:29])[CH2:27][CH2:28]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70874027HCID 70874027, compound

Product 1

HCID 70874001HCID 70874001, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(4-oxocyclohexyl)amino)-2-methylbenzamide (0.30 g, 0.68 mmol) in MeOH was added NaBH4 (0.038 g, 1.01 mmol) slowly at 0° C. The resulting reaction mixture was stirred at 0° C. for 2 h. On completion, the reaction was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with water, dried, concentrated under reduced pressure and the crude material obtained was purified by acetonitrile and ether washings to afford the title compound as a mixture of isomers (175 mg, 58%). LCMS: 446.35 (M+1)+; HPLC: 74.32% & 24.18% (@ 210-370 nm) (Rt; 5.157 & 5.276); Method: Column: YMC ODS-A 150 mm×4.6 mm×5μ; Mobile Phase: A; 0.05% TFA in water/B; 0.05% TFA in acetonitrile; Inj. Vol: 10 μL, Col. Temp.: 30° C.; Flow rate: 1.4 mL/min.; Gradient: 5% B to 95% B in 8 min, Hold for 1.5 min, 9.51-12 min 5% B); 1H NMR (DMSO-d6, 400 MHz) δ 11.49 (s, 1H), 8.25 (s, 1H), 7.17 (s, 1H), 6.96 (s, 1H), 5.86 (s, 1H), 4.25 (d, 2H, J=4 Hz), 3.33 (m, 1H), 3.04 (m, 2H), 2.19 (s, 3H), 2.14 (s, 3H), 2.10 (s, 3H), 1.78 (m, 2H), 1.66 (m, 2H), 1.38 (m, 3H), 1.10 (m, 2H), 0.78 (t, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customOn completion, the reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customthe crude material obtained
  8. customwas purified by acetonitrile and ether washings

Sources & evidence

ORD record
ord-2147e599ab984a6ead580a85f6917f11
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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