Dimethylamine → N-(5-cyanopyridin-2-yl)-7-(dimethoxymethyl)-6-((dimethylamino)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1777891Notes

Reaction equation

HRID 1777891 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([CH:27]=O)=[C:19]([CH:22]([O:25][CH3:26])[O:23][CH3:24])[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2].[CH3:29][NH:30][CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([CH2:27][N:30]([CH3:31])[CH3:29])=[C:19]([CH:22]([O:23][CH3:24])[O:25][CH3:26])[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 118037054N-(5-cyanopyridin-2-yl)-7-(dimethoxymethyl)-6-formyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide2×

Product 1

HCID 118036819N-(5-cyanopyridin-2-yl)-7-(dimethoxymethyl)-6-((dimethylamino)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(5-cyanopyridin-2-yl)-7-(dimethoxymethyl)-6-formyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 36, 25 mg, 0.066 mmol) and dimethylamine (7.9 M in water, 0.017 ml, 0.131 mmol) in DCM (0.5 ml) was added sodium triacetoxyborohydride (27.8 mg, 0.131 mmol). The reaction mixture was stirred at room temperature for 1 h, poured into sat. aq. NaHCO3 and extracted with DCM (3×). The combined organic phases were dried over Na2SO4, filtered and concentrated. The crude material was purified by supercritical fluid chromatography (SFC 1, NH2 column) to give the title compound as a colorless solid. (UPLC-MS 3) tR 0.73 min; ESI-MS 411.2 [M+H]+.

Workup

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by supercritical fluid chromatography (SFC 1, NH2 column)

Sources & evidence

ORD record
ord-4a202ba6646a426798a6764665b474a1
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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