Dimethylformamide → 1-(6-Amino-pyridin-2-ylmethyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

HRID 227141Notes

Reaction equation

HRID 227141 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:27][C:28](=[N:30][C:31]([NH:33]C(=O)C(F)(F)F)=[CH2:32])[CH3:29].[CH3:40]N(C=O)C>>[NH2:33][C:31]1[N:30]=[C:28]([CH2:29][N:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22](=[O:23])[C:13]([C:11]([C:9]3[CH:8]=[CH:7][C:6]4[O:1][CH2:2][CH2:3][O:4][C:5]=4[CH:10]=3)=[O:12])=[CH:14]2)[CH:27]=[CH:40][CH:32]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 577545433-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-oneHCID 86613650N-[1-(2-Bromo-1-methyl-ethylideneamino)-vinyl]-2,2,2-trifluoro-acetamide

Product 1

HCID 577547311-(6-Amino-pyridin-2-ylmethyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

Procedure

The mixture of 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one 70 mg (0.228 mmol) in DMF (1 mL) and sodium hydride 11.8 mg (0.296 mmol ) was stirred at room temperature for 60 min, followed by the addition of N-[1-(2-Bromo-1-methyl-ethylideneamino)-vinyl]-2,2,2-trifluoro-acetamide 83.8 mg (0.296 mmol). The mixture was stirred for 60 min, quenched with water, taken up with ethyl acetate, dried over sodium sulfate and purified with flash chromatography. The purified product was treated with Diethylamine in methanol over weekend, filtered to give the desired product 10 mg. LCMS observed for (M+H)+: 414.

Workup

  1. stirringThe mixture was stirred for 60 min
  2. customquenched with water
  3. dry with materialdried over sodium sulfate
  4. custompurified with flash chromatography
  5. additionThe purified product was treated with Diethylamine in methanol over weekend
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b510273cbc914de985461e85875d6ba7
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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