3,3,3-Trifluoropropionic acid → HCID 15948038, compound

HRID 1466409Notes

Reaction equation

HRID 1466409 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]=[C:38]([Cl:40])[CH:37]=[CH:36][C:35]=5[Cl:41])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[N: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:41][C:35]1[CH:36]=[CH:37][C:38]([Cl:40])=[CH:39][C:34]=1[N:26]1[CH:27]=[C:28]([C:30]([F:31])([F:33])[F:32])[N:29]=[C:25]1[C:22]1[S:21][C:20]([C:17]2[CH:18]=[CH:19][C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[N:15][CH:16]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 27779723,3,3-Trifluoropropionic acidHCID 15948037HCID 15948037, compound

Product 1

HCID 15948038HCID 15948038, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(5-{5-[1-(2,5-Dichloro-phenyl)-4-trifluoromethyl-1H-imidazol-2-yl]-thiophen-2-yl}-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (104 mg, 0.17 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. The residue was precipitated from dichloromethane/Hexane mixture, then filtered and washed several times with dichloromethane to give yellow solid (50 mg, 57% yield). 1H-NMR. (400 MHz, CDCl3): δ 3.30-2.97 (m, 4H), 3.57-3.54 (m, 4H), 6.63 (d, J=8.7, 1H), 6.78 (d, J=4.0, 1H), 6.96 (d, J=4.0, 1H), 7.31 (s, 1H), 7.60-7.50 (m, 4H), 8.37 (m, 1H). MS (ES): 524.3, 526.5, [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. customThe residue was precipitated from dichloromethane/Hexane mixture
  7. filtrationfiltered
  8. washwashed several times with dichloromethane

Sources & evidence

ORD record
ord-9246ca718ba6478bb91e4d1784017c08
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

Loading…