Sodium borohydride → HCID 21073761, compound

HRID 1373564Notes

Reaction equation

HRID 1373564 reaction equation
[O:1]=[C:2]1[CH2:11][C:10]2[C:9]([N:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]4[N:32]=[C:31]5[C:26]([CH:27]=[CH:28][C:29](=[O:33])[NH:30]5)=[CH:25][CH:24]=4)[CH2:14][CH2:13]3)=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([N:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]4[N:32]=[C:31]5[C:26]([CH:27]=[CH:28][C:29](=[O:33])[NH:30]5)=[CH:25][CH:24]=4)[CH2:16][CH2:17]3)=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21073767HCID 21073767, compound

Product 1

HCID 21073761HCID 21073761, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-{4-[4-(7-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl)-piperazin-1-yl]-butoxy}-1H-[1,8]naphthyridin-2-one (1.20 g, 2.69 mmol) in methanol (10 mL) was added portionwise NaBH4 (0.41 g, 10.76 mmol). The reaction mixture was stirred at room temperature for 30 min and quenched with saturated NH4Cl solution and the compound was extracted with CH2Cl2 (2×20 mL). The organic layer was washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude product was purified by column chromatography (10% methanol in ethyl acetate) to afford the title compound (0.60 g, 50%), as a white solid. 1H NMR (400 MHz, CDCl3) δ 9.25 (s, 1H), 7.72 (d, 1H), 7.63 (d, 1H), 7.12 (t, 1H), 6.91 (d, 1H), 6.85 (d, 1H), 6.59 (d, 1H), 6.52 (d, 1H), 4.23 (t, 2H), 4.13–4.08 (m, 1H), 3.25–3.20 (m, 1H), 3.02–2.83 (m, 6H), 2.61–2.47 (m 6H), 1.88–1.71 (m, 6H). ES MS: 449.26 (M+1)+ (Exact mass: 448.25).

Workup

  1. customquenched with saturated NH4Cl solution
  2. extractionthe compound was extracted with CH2Cl2 (2×20 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography (10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-a436e1183464429b98899551e534000a
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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