Morpholine → HCID 11453778, compound

HRID 2216309Notes

Reaction equation

HRID 2216309 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12]([NH:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])=[N:13][C:14]([CH3:17])=[N:15][CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[CH3:17][C:14]1[N:13]=[C:12]([NH:18][C:19]2[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=2[CH3:27])[C:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 11485961HCID 11485961, compound

Product 1

HCID 11453778HCID 11453778, compoundYield 92%

Procedure

A mixture of [5-(4-fluoro-benzenesulfonyl)-2-methyl-pyrimidin-4-yl]-(2,4,6-trimethylphenyl)-amine (100 mg, 0.26 mmol) and morpholine (5 mL) was heated at reflux under N2 for 2 h, and then cooled to room temperature. The mixture was concentrated in vacuo, and the residue was dissolved in EtOAc, washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (EtOAc) to provide the target compound (108 mg, 92%) as a white solid: mp 221–223° C.; 1H NMR (500 MHz, CDCl3) δ 8.71 (s, 1H), 8.24 (br s, 1H), 7.80 (d, J=9.0 Hz, 2H), 6.91 (s, 2H), 6.88 (d, J=9.0 Hz, 2H), 3.83 (t, J=5.0 Hz, 4H), 3.29 (t, J=5.0 Hz, 4H), 2.37 (s, 3H), 2.30 (s, 3H), 2.03 (s, 6H); APCI MS m/z 453 [(M+H)+, calcd for C24H29N4O3S, 453.2].

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 2 h
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-d8745014ac4548ffb2e6ae24b5bd8193
Source dataset
uspto-grants-2006_09
Patent number
US07112585B2

Reaction notes

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