Trifluoroacetic acid → HCID 178461856, compound

HRID 243082Notes

Reaction equation

HRID 243082 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C@H:15]2[CH2:18][C@@H:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16]2)[C:13]2[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([O:19][C@@H:17]1[CH2:18][C@H:15]([N:14]2[C:13]3[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:12]=3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178462193HCID 178462193, compound

Product 1

HCID 178461856HCID 178461856, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-[1-(cis-3-benzyloxycyclobutyl)-6-fluoro-1H-benzoimidazol-2-yl]ethyl]carbamic acid tert-butyl ester (570 mg, 1.3 mmol) in DCM (10 mL) was added TFA (4 mL) and the mixture stirred at RT for 1 h. The volatiles were removed in vacuo and the resulting residue dissolved in DCM and loaded onto SCX-2 (20 g). The cartridge was washed with DCM then MeOH and then 2M NH3 in MeOH solution. The relevant fractions were concentrated in vacuo to afford the title compound as yellow gum (320 mg, 73%). LCMS (Method J): RT 1.97 min [M+H]+ 340. 1H NMR (CDCl3, 400 MHz): δ 7.69-7.55 (2H, m), 7.44-7.24 (5H, m), 7.0 (1H, dt, J=11.8, 2.5 Hz), 4.81-4.66 (1H, m), 4.53 (2H, s), 4.32-4.21 (1H, m), 4.08-3.95 (1H, m), 3.02-2.75 (4H, m), 1.90 (2H, s, br), 1.50 (3H, d, J=7.0 Hz)-NMR: 328174

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe resulting residue dissolved in DCM
  3. washThe cartridge was washed with DCM
  4. concentrationThe relevant fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-eda6bb75f392461cbd1af4efa54e0354
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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