3,3,3-Trifluoropropionic acid → HCID 59632349, compound

HRID 2369048Notes

Reaction equation

HRID 2369048 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[S:21][C:22]([C:25]4[N:26]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[Cl:40])[N:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=4)=[CH:23][CH:24]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(CC(O)=O)(F)F>ClCCl>[Cl:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[N:26]1[C:25]([C:22]2[S:21][C:20]([C:17]3[CH:18]=[CH:19][C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[N:15][CH:16]=3)=[CH:24][CH:23]=2)=[CH:29][C:28]([C:30]([F:33])([F:31])[F:32])=[N:27]1

Participants

4

Reactant 2

HCID 27779723,3,3-Trifluoropropionic acidHCID 59633372HCID 59633372, compound

Product 1

HCID 59632349HCID 59632349, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(5-{5-[2-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-thiophen-2-yl}-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (196 mg, 0.33 mmol) was mixed with 4 mL 50% trifluoromethylacetic acid in dichloromethane, and stirred at room temperature for 2 hrs. All solvent was removed; the residue was redissolved in dichloromethane and neutralized to pH 7 by saturated NaHCO3. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give a solid that was washed several times with dichloromethane to give yellow solid (75 mg, 47% yield). 1H-NMR (400 MHz, CDCl3): δ 3.32-329 (m, 4H), 3.94-3.91 (m, 4H), 6.67 (d, J=8.8, 1H), 6.79 (d, J=3.8, 1H), 6.87 (s, 1H), 7.02 (d, J=3.8, 1H), 7.57-7.45 (m, 4H), 7.63 (dd, J=8.8, J=2.5, 1H), 8.34 (d, J=2.2, 1H). MS (ES) 490.3, 492.3, [M+H]+.

Workup

  1. customAll solvent was removed
  2. dissolutionthe residue was redissolved in dichloromethane and neutralized to pH 7 by saturated NaHCO3
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a solid
  7. washthat was washed several times with dichloromethane

Sources & evidence

ORD record
ord-0fcac52630684f968e3d575a5d27b7d0
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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