Trifluoroacetic acid → 1-(2-chloro-phenyl)-5-[4-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole trifluoroacetate

HRID 2207958Notes

Reaction equation

HRID 2207958 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][CH:24]=3)=[CH:15][CH:14]=2)[CH2:11][C:10]([C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])=[N:9]1.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>ClCCl>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH:24]=3)=[CH:17][CH:18]=2)[CH2:11][C:10]([C:32]([F:38])([F:37])[C:33]([F:34])([F:35])[F:36])=[N:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1184320161-(2-chloro-phenyl)-5-[4-(1-BOC-1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 1184317931-(2-chloro-phenyl)-5-[4-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole trifluoroacetateYield 105.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-chloro-phenyl)-5-[4-(1-BOC-1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (630 mg, 1.13 mmol) prepared in Example 9 in dichloromethane (6 mL), was slowly added trifluoroacetic acid (867.0 uL, 11.33 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 hour and then concentrated under reduced pressure to give 680.0 mg of the titled compound as a yellow liquid.

Workup

  1. customat 0° C
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0e5d9a3a5af4392aec71bbd455ae6bb
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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