Sodium borohydride → HCID 21073544, compound

HRID 1373600Notes

Reaction equation

HRID 1373600 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[N:29]=[C:28]3[C:23]([C:24](=[O:33])[C:25]([CH3:32])([CH3:31])[C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[N:29]=[C:28]3[C:23]([CH:24]([OH:33])[C:25]([CH3:31])([CH3:32])[C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21073534HCID 21073534, compound

Product 1

HCID 21073544HCID 21073544, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butoxy}-3,3-dimethyl-1H-[1,8]naphthyridine-2,4-dione (0.132 g, 0.268 mmol) in THF (2 mL), cooled to 0° C. was added NaBH4 (0.013 g, 0.335 mmol). The reaction was warmed to room temperature and stirred for 3 hours. The reaction was quenched with saturated NaHCO3 and partitioned between EtOAc and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give the title compound as a white solid (0.095 g, 0.192 mmol, 57%). MS: APCI: M+1: 493.1 (Exact Mass: 492.17).

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8e049d4a7dfd4692828e48074abe7bb5
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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