Formamidine acetate → HCID 178517945, compound

HRID 724472Notes

Reaction equation

HRID 724472 reaction equation
C([O:3][C:4]([C:6]1[C:10]([NH2:11])=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:7]=1)=O)C.C(O)(=O)C.[CH:30](N)=[NH:31]>C(OCCO)C>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[N:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[N:7]=[C:6]3[C:4]([OH:3])=[N:31][CH:30]=[N:11][C:10]=23)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 58747008HCID 58747008, compound

Product 1

HCID 178517945HCID 178517945, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 4-amino-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester I-2A-1a (19.27 g, 51.2 mmol) and formamidine acetate (15.99 g, 153.6 mmol) in 100 ml of 2-ethoxyethanol was refluxed for 3.5 hours under nitrogen. The reaction mixture was then cooled to room temperature and poured into ice-cold water. The yellow precipitate that formed was collected by filtration and washed with water. The solid was stirred in 45 ml methyl tert-butyl ether for 30 minutes. Cyclohexane (90 ml) was added, and the stirring was continued for another 45 minutes. The pale yellow solid was collected by filtration and dried to give 3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-ol I-2A-1b (17.55 g, 87%): MS 357.1 (M+1)+.

Workup

  1. additionpoured into ice-cold water
  2. customThe yellow precipitate that formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. additionCyclohexane (90 ml) was added
  6. waitthe stirring was continued for another 45 minutes
  7. filtrationThe pale yellow solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-f9af5ff6c35c4b7d813e14fb5056efd8
Source dataset
uspto-grants-2006_11
Patent number
US07141669B2

Reaction notes

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