Phosphorus oxychloride → 2-chloro-7-[3-(trifluoromethyl)pyridin-2-yl]-N-[5-(trifluoromethyl) pyridin-2-yl]-[1,8]naphthyridin-4-amine

HRID 1724842Notes

Reaction equation

HRID 1724842 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[C:4]([C:9]2[N:18]=[C:17]3[C:12]([C:13]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=4)=[CH:14][C:15](O)=[N:16]3)=[CH:11][CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.P(Cl)(Cl)([Cl:35])=O>>[Cl:35][C:15]1[CH:14]=[C:13]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=2)[C:12]2[C:17](=[N:18][C:9]([C:4]3[C:3]([C:2]([F:32])([F:31])[F:1])=[CH:8][CH:7]=[CH:6][N:5]=3)=[CH:10][CH:11]=2)[N:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516409HCID 178516409, compound

Product 1

HCID 575611422-chloro-7-[3-(trifluoromethyl)pyridin-2-yl]-N-[5-(trifluoromethyl) pyridin-2-yl]-[1,8]naphthyridin-4-amine

Procedure

Heat 7-[3-(trifluoromethyl)pyridin-2-yl]-4-{[5-(trifluoromethyl)pyridin-2-yl]amino}-[1,8]naphthyridin-2-ol (112 mg) and phosphorus oxychloride (1 mL) at reflux for 1 hour. Evaporate to dryness, partition between ethyl acetate and saturated aqueous NaHCO3 and extract with EtOAc. Dry the combined organics over Na2SO4, concentrate under vacuum to obtain the title compound.

Workup

  1. temperatureat reflux for 1 hour
  2. customEvaporate to dryness
  3. custompartition between ethyl acetate and saturated aqueous NaHCO3
  4. extractionextract with EtOAc
  5. dry with materialDry the combined organics over Na2SO4
  6. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-ce3901480faa4588900d52cfcf7c94b6
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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