Potassium Carbonate → HCID 22050389, compound

HRID 1867166Notes

Reaction equation

HRID 1867166 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([NH2:22])=[O:21])[CH:15]=2)[C:8](=[O:13])[CH:9]=[C:10]([OH:12])[CH:11]=1)(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[F:29][C:30]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:31]=1[CH2:32]Br>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([NH2:22])=[O:21])[CH:15]=2)[C:8](=[O:13])[CH:9]=[C:10]([O:12][CH2:32][C:31]2[CH:34]=[CH:35][C:36]([F:38])=[CH:37][C:30]=2[F:29])[CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54724225{1-[3-(aminocarbonyl)phenyl]-4-hydroxy-6-oxo-1,6-dihydropyridin-2-yl}methyl Acetate

Product 1

HCID 22050389HCID 22050389, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

{1-[3-(aminocarbonyl)phenyl]-4-hydroxy-6-oxo-1,6-dihydropyridin-2-yl}methyl acetate (crude from step 1) (3.61 g, 11.94 mmol) was dissolved in N,N-dimethylformamide (40 mL). K2CO3 (3.80 g, 27.46 mmol) was added followed by 2,4-difluorobenzyl bromide (5.44 g, 26.27 mmol). The reaction mixture was stirred for 48 hours at room temperature. The reaction mixture was then partially concentrated and the residue taken up in dichloromethane/tetrahydrofuran 1:1 and filtered. The filtrate was collected, concentrated and the residue tritrated with dichloromethane to afford a tan solid (1.64 g, 32%). 1H NMR (400 MHz, DMF-d6) δ 8.19 (br s, 1H), 8.07 (app dt, J=1.35, 7.66 Hz, 1H), 7.91 (app t, J=1.81 Hz, 1H), 7.76 (app dt, J=6.58, 8.59 Hz, 1H) 7.62 (t, J=7.79 Hz, 1H), 7.55 (ddd, J=1.21, 2.01, 7.79 Hz, 1H), 7.46 (br s, 1H), 7.34 (ddd, J=2.55, 9.40, 10.47 Hz, 1H), 7.23-7.18 (m, 1H), 6.26 (d, J=2.55 Hz, 1H), 6.11 (d, J=2.69 Hz, 1H), 5.23 (s, 2H), 4.62 (AB q, JAB=14.97 Hz, 2H), 1.96 (s, 3H). ES-HRMS m/z 429.1280 (M+H calcd for C22H18F2N2O5 requires 429.1257).

Workup

  1. concentrationThe reaction mixture was then partially concentrated
  2. filtrationfiltered
  3. customThe filtrate was collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe196fd7c7f24813a731c39be6f32f71
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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