Sodium hydride → 5-(Pyrrolidi n-2-on-4-yl-methylhydroxy)-7-(4-dimethylamino-3-methylphenyl)-[1,6]naphthyridine

HRID 1850806Notes

Reaction equation

HRID 1850806 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][NH:6][C:5](=[O:8])[CH2:4]1.[H-].[Na+].Cl[C:12]1[N:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[C:24]([CH3:31])[CH:23]=2)[CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2>CC(N(C)C)=O>[NH:6]1[CH2:7][CH:3]([CH2:2][O:1][C:12]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[C:24]([CH3:31])[CH:23]=3)[CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[N:17]3)[CH2:4][C:5]1=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 152563274-Hydroxymethyl-pyrrolidin-2-oneHCID 446328825-Chloro-7-(4-dimethylamino-3-methylphenyl)-[1,6]naphthyridine

Product 1

HCID 584831155-(Pyrrolidi n-2-on-4-yl-methylhydroxy)-7-(4-dimethylamino-3-methylphenyl)-[1,6]naphthyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

45 mg (0.38 mmol) 4-hydroxymethylpyrrolidin-2-one was placed in 1 ml dimethylacetamide and 16 mg (0.29 mmol) sodium hydride (60%) were added and the mixture was stirred for 15 min at ambient temperature. Then 100 mg (0.34 mmol) of 6.1 was added and the mixture was stirred for 2 h at 50° C. and overnight at 25° C. The reaction mixture was purified by chromatography (RP-HPLC-MS). The corresponding fractions were freeze-dried.

Workup

  1. stirringthe mixture was stirred for 2 h at 50° C. and overnight at 25° C
  2. customThe reaction mixture was purified by chromatography (RP-HPLC-MS)
  3. customThe corresponding fractions were freeze-dried

Sources & evidence

ORD record
ord-bbfe9fb34fa944559d6e3906dd6287a0
Source dataset
uspto-grants-2015_02
Patent number
US08957088B2

Reaction notes

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