Hydrogen Bromide → HCID 178433426, compound

HRID 899311Notes

Reaction equation

HRID 899311 reaction equation
C(O[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:5])C.C([CH2:33][C:34](=[NH:36])[S-])C1C=CC=CC=1.Br>N1C=CC=CC=1>[Cl:18][C:15]1[CH:16]=[CH:17][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:5])=[N:36][C:34]([CH3:33])=[N:11][C:10]=23)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 17957426HCID 17957426, compound2×HCID 58747008HCID 58747008, compound

Product 1

HCID 178433426HCID 178433426, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 4-amino-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester I-2A-1a (21.4 g, 57 mmol) and benzylthioacetimidate.HBr (12.6 g, 51 mmol) in pyridine was heated at 115° C. (see Yuan et al., Bioorg. & Med. Chem. Lett., 12, 2133-2136 (2002)). Additional benzylthioacetimidate.HBr (12.6 g) was added after 0.5 h and 1.5 h. The reaction mixture was stirred for an additional 1 h at 115° C. After cooling to room temperature, a yellow solid precipitated out of solution. The reaction mixture was poured over ice water and acidified with conc. HCl (210 ml). Additional ice was added to keep the reaction mixture cool. The yellow solid was collected by filtration and washed with H2O to give the desired product, I-4A-1a (24 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. customa yellow solid precipitated out of solution
  3. additionThe reaction mixture was poured over ice water
  4. additionAdditional ice was added
  5. temperaturecool
  6. filtrationThe yellow solid was collected by filtration
  7. washwashed with H2O

Sources & evidence

ORD record
ord-0b15069fc7614492a02fc29a79712641
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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