Ammonia → HCID 22386475, compound

HRID 2119306Notes

Reaction equation

HRID 2119306 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:4][N:3]=1.[F:21][C:22]([F:32])([F:31])[C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[Cl:30])[NH2:26].N.O>C(O)C.Cl.O1CCOCC1>[Cl:30][C:29]1[CH:28]=[CH:27][C:25]([NH:26][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][CH2:13][CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[N:4][N:3]=2)=[CH:24][C:23]=1[C:22]([F:21])([F:31])[F:32]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 22386479HCID 22386479, compound

Product 1

HCID 22386475HCID 22386475, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 321 mg (1.13 mmol) 1-chloro-4-[3-(pyridin-3-yl)propyl]phthalazine, 243 mg (1.24 mmol) 3-trifluoromethyl-4-chloroaniline in 6 ml ethanol and 0.28 ml 4 N HCl in dioxane is stirred for 100 min at 60° C. The cooled reaction solution is poured onto a mixture of 2 ml sat. NH3 solution and 20 ml water and extracted immediately 3 times with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; EtOAc/acetone 9:1) and stirring in EtOAc/DIPE yield the title compound: m.p. 165-166° C.; TLC (EtOAc/acetone 9:1) Rf=0.21; 1H-NMR (DMSO-d6) 9.50 (s, HN), 8.58 (m, 2H), 8.47 (s, 1H), 8.39 (dd, 1H), 8.33 (dd, 1H), 8.16 (d, 1H), 8.01 (m, 2H), 7.67 (m, 2H), 7.30 (dd, 1H), 3.22 (t, 2H), 2.76 (t, 2H), 2.11 (quint., 2H); FAB-MS (M+H)+=443; an. calc. (C23H18N4ClF3) C, 62.38%; H, 4.10%; N, 12.65%; Cl, 8.01%; F, 12.87%; meas. C, 62.41%; H, 4.07%; N, 12.58%; Cl, 7.99%; F, 12.84%.

Workup

  1. customThe cooled reaction solution
  2. extractionextracted immediately 3 times with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-987bc90b0e334cafb0d290d743eaead6
Source dataset
uspto-grants-2004_02
Patent number
US06686347B2

Reaction notes

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