Sodium triacetoxyborohydride → 7-{4-[4-(1,3-Dihydro-isobenzofuran-4-yl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-one

HRID 1373634Notes

Reaction equation

HRID 1373634 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[CH2:4][CH2:3]1.[CH2:18]1[C:26]2[C:21](=[C:22]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:23]=[CH:24][CH:25]=2)[CH2:20][O:19]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[CH2:18]1[C:26]2[C:21](=[C:22]([N:27]3[CH2:32][CH2:31][N:30]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:8]4[N:9]=[C:10]5[C:5]([CH2:4][CH2:3][C:2](=[O:1])[NH:11]5)=[CH:6][CH:7]=4)[CH2:29][CH2:28]3)[CH:23]=[CH:24][CH:25]=2)[CH2:20][O:19]1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 210731161-(1,3-Dihydro-isobenzofuran-4-yl)-piperazineHCID 210733774-((7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)oxy)butanal

Product 1

HCID 210734857-{4-[4-(1,3-Dihydro-isobenzofuran-4-yl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-oneYield 31.8%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.278 g, 1.186 mmol, 1.1 eq) and 1-(1,3-dihydro-isobenzofuran-4-yl)-piperazine (0.217 g, 1.064 mmol, 1 eq) in dichloroethane (5 mL) was added NaBH(OAc)3 (0.469 g, 4.425 mmol, 3.73 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 1 N HCl in ether provided the title compound (0.143 g, 26%). CHN Found: C, 64.37; H, 6.54; N, 12.13. This calculates out for C24H30N4O3×1.00 HCl.

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-a5231a57289a471daccb6d8b7322c95a
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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