N,N-Diethylaniline → HCID 86597651, compound

HRID 1786307Notes

Reaction equation

HRID 1786307 reaction equation
[CH:1]1([C:8]2[N:13]3[N:14]=[CH:15][N:16]=[C:12]3[N:11]=[C:10](O)[C:9]=2[C:18]2[C:23]([F:24])=[CH:22][C:21]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)=[CH:20][C:19]=2[F:39])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:42])=O.C(N(CC)C1C=CC=CC=1)C>>[Cl:42][C:10]1[C:9]([C:18]2[C:19]([F:39])=[CH:20][C:21]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)=[CH:22][C:23]=2[F:24])=[C:8]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)[N:13]2[N:14]=[CH:15][N:16]=[C:12]2[N:11]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178491462HCID 178491462, compound

Product 1

HCID 86597651HCID 86597651, compound

Procedure

To the above 7-cycloheptyl-6-(2,6-difluoro-4-{3-[(4-methoxybenzyl)oxy]propoxy}phenyl)[1,2,4]triazolo[1,5-a]pyrimidin-5-ol (820 mg) is added 5 mL of phosphorous oxychloride and 2 mL of N,N-diethylaniline, and the mixture is heated at reflux for 1 h. The excess phosphorous oxychloride is removed in vaccuo, and the resulting residue is partitioned between methylene chloride and 1 N hydrochloric acid. The organic layer is washed with saturated sodium chloride, dried over magnesium sulfate, and concentrated to a residue. The residue is chromatographed over silica gel, eluting with a gradient of hexanes to 20% ethyl acetate in hexanes. Concentration provides 5-chloro-7-cycloheptyl-6-(2,6-difluoro-4-{3-[(4-methoxybenzyl)oxy]propoxy}phenyl)[1,2,4]triazolo[1,5-a]pyrimidine as a yellow oil (180 mg). MS: m/z 557.2 (M+H).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 1 h
  3. customThe excess phosphorous oxychloride is removed in vaccuo
  4. customthe resulting residue is partitioned between methylene chloride and 1 N hydrochloric acid
  5. washThe organic layer is washed with saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to a residue
  8. customThe residue is chromatographed over silica gel
  9. washeluting with a gradient of hexanes to 20% ethyl acetate in hexanes
  10. concentrationConcentration

Sources & evidence

ORD record
ord-c65bec13f6af40bfa291e2b9ee177f76
Source dataset
uspto-grants-2009_03
Patent number
US07507739B2

Reaction notes

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