Triethylamine → HCID 21073790, compound

HRID 1373647Notes

Reaction equation

HRID 1373647 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.Cl.Cl.[O:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][C:28]=2[N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH2:23][CH2:22][CH2:21]1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CN(C=O)C>[O:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][C:28]=2[N:30]2[CH2:35][CH2:34][N:33]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:8]3[N:9]=[C:10]4[C:5]([CH:4]=[CH:3][C:2](=[O:1])[NH:11]4)=[CH:6][CH:7]=3)[CH2:32][CH2:31]2)[CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 21073191HCID 21073191, compoundHCID 210733804-(7-Oxo-7,8-dihydro-1,8-naphthyridin-2-yloxy)butanal

Product 1

HCID 21073790HCID 21073790, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(7-oxo-7,8-dihydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (300 mg, 1.29 mmol) and 1-chroman-8-yl-piperazine bishydrochloride (395 mg, 1.36 mmol) were suspended in DCE (8 mL)/DMF (1 mL) and Et3N (0.54 mL, 3.88 mmol) was added. After about 10 min, NaBH(OAc)3 (356 mg, 1.68 mmol) was added and the reaction was stirred at room temperature for 2 h. The reaction was quenched with saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated. Purification by liquid chromatography (5% MeOH/CH2Cl2 with 0.5% NH4OH) gave the title compound as a white foam (364 mg, 0.838 mmol, 65%). The foam was dissolved in THF/Et2O and 1 N HCl in Et2O (0.84 mL) was added. The resulting precipitate was collected by filtration, washed with Et2O and dried to give a white solid (368 mg). MS: APCI: M+1: 435.2 (Exact mass: 434.23).

Workup

  1. additionwas added
  2. customThe reaction was quenched with saturated NaHCO3
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by liquid chromatography (5% MeOH/CH2Cl2 with 0.5% NH4OH)

Sources & evidence

ORD record
ord-f81f3aa4161e4998b34febfd03770d9a
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

Loading…