Sodium triacetoxyborohydride → HCID 178515657, compound

HRID 1373653Notes

Reaction equation

HRID 1373653 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH:16]=O)[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1.[N:18]1([C:24]2[C:32]3[N:31]=[C:30]([C:33]([F:36])([F:35])[F:34])[NH:29][C:28]=3[CH:27]=[CH:26][CH:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[F:36][C:33]([F:34])([F:35])[C:30]1[NH:31][C:32]2[C:24]([N:18]3[CH2:19][CH2:20][N:21]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:8]4[N:9]=[C:10]5[C:5]([CH:4]=[CH:3][C:2](=[O:1])[NH:11]5)=[CH:6][CH:7]=4)[CH2:22][CH2:23]3)=[CH:25][CH:26]=[CH:27][C:28]=2[N:29]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 18414107HCID 18414107, compoundHCID 210733804-(7-Oxo-7,8-dihydro-1,8-naphthyridin-2-yloxy)butanal

Product 1

HCID 178515657HCID 178515657, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-(7-oxo-7,8-dihydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.211 g, 0.908 mmol, 1.29 eq) and 4-piperazin-1-yl-2-trifluoromethyl-1H-benzoimidazole (0.190 g, 0.703 mmol, 1 eq) in dichloroethane (5 mL) was added NaBH(OAc)3 (0.558 g, 2.631 mmol, 3.74 eq). The slurry was allowed to stir overnight at room temperature (18 h). The mixture was diluted with EtOAc and quenched with saturated NaHCO3. The organic phase was then washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. Purification by silica gel chromatography (2% MeOH/CH2Cl2) followed by formation of the HCl salt using 1N HCl in ether provided the title compound (0.230 g, 62%). MS: APCI: M+1: 487.1 (Exact Mass: 486.20).

Workup

  1. customquenched with saturated NaHCO3
  2. washThe organic phase was then washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by silica gel chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d1a6bfc33834416f9bc9966c3fdec6b2
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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