Trifluoroacetic acid → HCID 178457790, compound

HRID 518679Notes

Reaction equation

HRID 518679 reaction equation
[F:1][C:2]1[CH:41]=[CH:40][C:5]([C:6]([NH:8][C:9]2[N:13]([C@H:14]3[CH2:19][CH2:18][C@@H:17]([C:20](=[O:25])[NH:21][CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]3)[C:12]3[CH:26]=[C:27]([O:30]CC4C=CC(OC)=CC=4)[CH:28]=[CH:29][C:11]=3[N:10]=2)=[O:7])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[N:13]([C@H:14]3[CH2:19][CH2:18][C@@H:17]([C:20](=[O:25])[NH:21][CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]3)[C:12]3[CH:26]=[C:27]([OH:30])[CH:28]=[CH:29][C:11]=3[N:10]=2)=[O:7])=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 178491276HCID 178491276, compound

Product 1

HCID 178457790HCID 178457790, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-fluoro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(4-methoxybenzyloxy)-1H-benzo[d]imidazol-2-yl)benzamide (232 mg, 0.415 mmol) in DCM was added TFA (0.96 mL, 1.246 mmol), and the mixture was stirred at RT for 90 minutes. Additional TFA (0.96 mL, 1.246 mmol) was added, and the mixture was stirred at RT for 1 hour longer. The mixture was diluted with DCM, washed with 1 N aqueous NaOH, and the water layer back-extracted with DCM. The aqueous layer was adjusted to pH 8, and the pale green solid was collected and rinsed with 2 mL water. The solid was dissolved in ether and washed with brine, dried over Na2SO4, filtered, and evaporated. The title compound was obtained as a white sold (153 mg, 84% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (d, J=8 Hz, 6H) 1.59 (m, 2H) 1.65-1.82 (m, 2H) 2.02-2.19 (m, 2H) 2.46-2.58 (m, 1H) 2.62-2.79 (m, 2H) 3.93-4.07 (m, 1H) 4.70-4.85 (m, 1H) 6.67 (dd, J=8.61, 2.15 Hz, 1H) 7.03 (d, J=2.05 Hz, 1H) 7.14-7.28 (m, 2H) 7.33 (d, J=8.51 Hz, 1H) 7.64 (d, J=7.82 Hz, 1H) 8.16-8.38 (m, 2H) 9.40 (s, 1H) 12.58 (s, 1H). M/Z calc'd for C24H27FN4O3: 438.50. found 439 [M+H].

Workup

  1. stirringthe mixture was stirred at RT for 1 hour longer
  2. washwashed with 1 N aqueous NaOH
  3. extractionthe water layer back-extracted with DCM
  4. customthe pale green solid was collected
  5. washrinsed with 2 mL water
  6. dissolutionThe solid was dissolved in ether
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-7f1c3b72e4a04da69d02bc7a25bd57c7
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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