Water → HCID 178488684, compound

HRID 860751Notes

Reaction equation

HRID 860751 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=C[CH:2]=1.[NH2:12][C:13]1[N:17]([C:18]([NH2:20])=[O:19])[N:16]=[C:15]([CH3:21])[C:14]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[CH3:30].C(OC)(OC)(OC)C.O>C(#N)C>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:14]2[C:15]([CH3:21])=[N:16][N:17]3[C:18]([OH:19])=[N:20][C:1]([CH3:2])=[N:12][C:13]=23)=[C:23]([CH3:30])[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 15050Trimethyl orthoacetateHCID 58766002HCID 58766002, compound

Product 1

HCID 178488684HCID 178488684, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

p-Toluenesulfonic acid (29.2 g, 154 mmol) in acetonitrile (100 mL) was added to the reaction mixture described in Example 3 containing 5-amino-4-(4-methoxy-2-methylphenyl)-3-methylpyrazole-1-carboxylic acid amide. The resulting mixture was heated to 85–90° C. and trimethyl orthoacetate (160 mL, 1.26 mol) was added over 5 minutes during the heating. The reaction was held for about 45 minutes in the desired range with a total of 1.5 hours of heating time from the initiation of the heating cycle. Reaction progress was monitored by HPLC. Water (1.50 L) was added over 5 minutes with a temperature drop to about 60° C. The resulting mixture was cooled to about 20° C. over 1 hour and the product isolated by filtration. The yield was 136 g (78.0% with a purity of 99.5 A %).

Workup

  1. temperatureThe resulting mixture was heated to 85–90° C.
  2. temperaturein the desired range with a total of 1.5 hours of heating time from the initiation of the heating cycle
  3. customReaction progress
  4. customthe product isolated by filtration

Sources & evidence

ORD record
ord-b26239fcb88942ffa0975a3784344a51
Source dataset
uspto-grants-2006_12
Patent number
US07153961B2

Reaction notes

Loading…