Potassium Carbonate → HCID 54575576, compound

HRID 1519248Notes

Reaction equation

HRID 1519248 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[O:6][C:7]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=1.[CH3:23][NH:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([S:8][C:7]2[O:6][C:5]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:4][C:3]=2[CH2:2][N:24]([CH3:23])[C:25]2[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 140375Methyl 4-methylaminobenzoateHCID 67452891HCID 67452891, compound2×

Product 1

HCID 54575576HCID 54575576, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-{[4-(bromomethyl)-2-(4-fluorophenyl)-1,3-oxazol-5-yl]sulfanyl}-5-chloropyridine (intermediate B3.1, 0.03 g, 0.075 mmol), methyl 4-methylaminobenzoate (0.013 g, 0.08 mmol) and K2CO3 (0.03 g, 0.225 mmol) in DMF was heated at 65° C. for 2 hr, filtered and purified by reverse phase HPLC to give methyl 4-[({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methyl)(methyl)amino]benzoate. 1H NMR (400 MHz, CDCl3) δ 8.31 (d, J=2.5 Hz, 1H), 8.03 (m, 2H), 7.72 (d, J=9.2 Hz, 2H), 7.34 (dd, J=8.4, 2.5 Hz, 1H), 7.13 (m, 2H), 6.70 (m, 3H), 4.62 (s, 2H), 3.84 (s, 3H), 3.17 (s, 3H); HRMS exact mass calc for C24H19ClFN3O3S [M+H]+: 484.0892; observed: 484.0890.

Workup

  1. filtrationfiltered
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-577b205845ec4995802fc60ec9c58892
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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