4-Methylmorpholine → HCID 22051111, compound

HRID 1867115Notes

Reaction equation

HRID 1867115 reaction equation
[Br:1][C:2]1[C:3](=[O:29])[N:4]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][C:20]=2[Cl:28])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].ClC1N=C(OC)N=C(OC)[N:32]=1.CN1CCOCC1.[NH4+].[OH-]>C1COCC1.O>[Br:1][C:2]1[C:3](=[O:29])[N:4]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([NH2:32])=[O:24])=[CH:21][C:20]=2[Cl:28])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 22050297HCID 22050297, compound

Product 1

HCID 22051111HCID 22051111, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4-[3-Bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-3-chlorobenzoic acid (0.5 g, 1.03 mmol) was taken up in THF (10 ml). 2-Chloro-4,6-dimethoxy-1,3,5-triazine (0.22 g, 1.24 mmol) and N-methyl morpholine (0.34 ml, 3.09 mmol) were added. The mixture stirred at room temperature for 1 hour. At this time, NH4OH (2.5 ml) was added and the reaction stirred at room temperature for one more hour. To the reaction mixture was added more THF (50 ml) and water (200 ml). The mixture was extracted with ethyl acetate. The ethyl acetate extraction was washed with saturated brine solution. The brine layer was extracted with ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was taken up in ethyl acetate and the resulting precipitate was collected on a filter pad to yield a white powder (0.38 g, 76%) 1H NMR (300 MHz, CD3OD) δ 8.18 (d, J=1.81 Hz, 1H), 8.02 (dd, J=8.26, 2.01 Hz, 1H), 7.69 (app q, J=8.26 Hz, 1H), 7.55 (d, J=8.06 Hz, 1H) 7.12-7.06 (m, 2H), 6.71 (s, 1H), 5.40 (s, 2H), 2.07 (s, 3H). ES MS m/z 482 (M+H). ES-HRMS m/z 482.9919 (M+H calcd for C20H15BrClF2N2O3 requires 482.9917).

Workup

  1. stirringthe reaction stirred at room temperature for one more hour
  2. extractionThe mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extraction
  4. washwas washed with saturated brine solution
  5. extractionThe brine layer was extracted with ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customthe resulting precipitate was collected on a filter pad

Sources & evidence

ORD record
ord-c9f121b4bd9e451f88bea9ddb00fba40
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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