Sodium triacetoxyborohydride → HCID 21073727, compound

HRID 1373541Notes

Reaction equation

HRID 1373541 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.[CH:18]1([C:21]2[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH:18]1([C:21]2[N:26]=[C:25]([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:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 21073175HCID 21073175, compoundHCID 210733774-((7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)oxy)butanal

Product 1

HCID 21073727HCID 21073727, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.47 g, 2.0 mmol) and 1-(6-cyclopropyl-pyridin-2-yl)-piperazine (0.41 g, 2.0 mmol) in dichloroethane (12 mL) was stirred for 20 min and NaBH(OAc)3 (0.55 g, 2.6 mmol) was added. The reaction was stirred at room temperature for 2.5 h. The reaction was quenched with saturated NaHCO3 and extracted with Et2O. The organic layer was washed with brine, dried over MgSO4 and concentrated. Purification by liquid chromatography (Biotage 12M, eluted with CHCl3) gave the title compound as an oil. The oil was dissolved in Et2O and treated with anhydrous HCl gas to give a precipitate. The mixture was filtered, washed with Et2O and hexanes and dried to give a white solid (121 mg). MS: APCI: M+1: 422.3 (Exact Mass: 421.25).

Workup

  1. stirringThe reaction was stirred at room temperature for 2.5 h
  2. customThe reaction was quenched with saturated NaHCO3
  3. extractionextracted with Et2O
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification
  8. washby liquid chromatography (Biotage 12M, eluted with CHCl3)

Sources & evidence

ORD record
ord-ee93530f1b0d473bb4442c8692b927d4
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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