Hydrochloric Acid → 3-[(3,4-difluorophenyl)amino]-5-(2,3-dihydro-1,4-benzodioxin-6-yl)-1H-pyrazole-1-acetic acid ethyl ester

HRID 1625118Notes

Reaction equation

HRID 1625118 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9]/[C:10](/SC)=[CH:11]/[C:12]([C:14]2[CH:23]=[CH:22][C:17]3[O:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)=O)[CH:5]=[CH:6][C:7]=1[F:8].[CH2:26]([O:28][C:29](=[O:33])[CH2:30][NH:31][NH2:32])[CH3:27].Cl.C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C>[CH2:26]([O:28][C:29](=[O:33])[CH2:30][N:31]1[C:12]([C:14]2[CH:23]=[CH:22][C:17]3[O:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)=[CH:11][C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[N:32]1)[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12509Acetic acid, 2-hydrazinyl-, ethyl esterHCID 66911477(2Z)-3-[(3,4-difluorophenyl)amino]-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(methylthio)-2-propen-1-one

Product 1

HCID 581888103-[(3,4-difluorophenyl)amino]-5-(2,3-dihydro-1,4-benzodioxin-6-yl)-1H-pyrazole-1-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of D16 (0.00138 mol), 2-hydrazinyl-acetic acid ethyl ester.monohydrochloride (1:1) (0.00276 mol) and K2CO3 (0.00206 mol) in t-BuOH (100 ml) was stirred at 85° C. overnight in a sealed reaction vessel. The reaction mixture was cooled, filtered and the filtrate's solvent evaporated in vacuo. Yield: 0.55 g of E10 (96.5%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate's solvent evaporated in vacuo

Sources & evidence

ORD record
ord-cbdfffc132fb4b6a9fd6b93ec5dd1fb3
Source dataset
uspto-grants-2014_07
Patent number
US08779158B2

Reaction notes

Loading…