Formamidine acetate → HCID 178517944, compound

HRID 899308Notes

Reaction equation

HRID 899308 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].C([O:10][C:11]([C:13]1[C:17](N)=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[N:15]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[N:14]=1)=O)C.C(OC(C1C(N)=C(C2C=CC(Cl)=CC=2)N(C2C=CC=CC=2Cl)N=1)=O)C>C(O)C>[Cl:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[N:15]1[C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][CH:20]=2)=[C:17]2[N:6]=[CH:5][N:7]=[C:11]([OH:10])[C:13]2=[N:14]1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 58747008HCID 58747008, compoundHCID 69204398HCID 69204398, compound

Product 1

HCID 178517944HCID 178517944, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of formamidine acetate (12.5 g, 0.12 mol) and 4-amino-1-(2-chlorophenyl)-5-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (4.77 g, 11.6 mmol; prepared using procedures and reagents analogous to those described above in the synthesis of 4-amino-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (I-2A-1a)) in ethanol (400 ml) was heated at reflux for 20 hours. The reaction was then cooled and concentrated in vacuo. The residue was extracted from water, adjusted to pH 3.5 using citric acid, with ethyl acetate, and the combined organic layers were washed with half saturated brine, dried (MgSO4), and concentrated in vacuo. Purification of the residue by silica gel chromatography using 10-50% ethyl acetate in hexanes as eluant afforded compound I-2A-2a (1.03 g, 23%) as a solid: APcl MS (M+1) 389.1; 1H NMR (CD3OD) δ 7.92 (s, 1H), 7.71-7.53 (m, 8H).

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for 20 hours
  4. temperatureThe reaction was then cooled
  5. concentrationconcentrated in vacuo
  6. extractionThe residue was extracted from water
  7. washwith ethyl acetate, and the combined organic layers were washed with half saturated brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customPurification of the residue by silica gel chromatography
  11. customafforded compound I-2A-2a (1.03 g, 23%) as a solid

Sources & evidence

ORD record
ord-ad14f6a33a014f888c18dd135c2603dc
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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