Triethylamine → HCID 21073733, compound

HRID 1373539Notes

Reaction equation

HRID 1373539 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1.CCN(CC)CC.[O:23]=[C:24]1[NH:33][C:32]2[N:31]=[C:30]([O:34][CH2:35][CH2:36][CH2:37][CH:38]=O)[CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[CH3:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:38][CH2:37][CH2:36][CH2:35][O:34][C:30]3[N:31]=[C:32]4[C:27]([CH2:26][CH2:25][C:24](=[O:23])[NH:33]4)=[CH:28][CH:29]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 3078152Piperazine, 1-(6-methyl-2-pyridinyl)-, dihydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 210733774-((7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)oxy)butanal

Product 1

HCID 21073733HCID 21073733, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-(6-methyl-pyridin-2-yl)-piperazine bishydrochloride (0.77 g, 3.08 mmol) in dichloroethane (10 mL) was added Et3N (1.0 mL, 7.17 mmol) and the mixture was stirred for 30 min. 4-(7-Oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.85 g, 3.63 mmol) was added as a solution in dichloroethane (3 mL) and the mixture was stirred at room temperature for 15 min. NaBH(OAc)3 (1.1 g, 5.2 mmol) was added as a solid and the mixture was stirred at room temperature for 3 h. The reaction was poured into EtOAc and washed with saturated NaHCO3 and brine, dried over MgSO4 and concentrated. The residue was partitioned between EtOAc and pH 4.5 aqueous citric acid. The product went into the aqueous layer selectively over the impurities. The aqueous layer was neutralized with solid NaHCO3 to pH 8 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated to give the title compound as a sticky foam (0.77 g). The foam was dissolved in Et2O and treated with anhydrous HCl gas to give a white precipitate. The mixture was filtered, washed with Et2O and hexanes, and dried to give a white solid (616 mg). MS: APCI: M+1: 396.1 (Exact Mass: 395.23).

Workup

  1. stirringthe mixture was stirred at room temperature for 15 min
  2. stirringthe mixture was stirred at room temperature for 3 h
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was partitioned between EtOAc and pH 4.5 aqueous citric acid
  7. extractionextracted with EtOAc
  8. washThe organic layer was washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-33afed8a95d04ca9af3bb7a6b358c749
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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