Trifluoroacetic acid → HCID 68157806, compound

HRID 242908Notes

Reaction equation

HRID 242908 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=2)[C:21]#[N:22])[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[N:11]=1)[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157429HCID 68157429, compound

Product 1

HCID 68157806HCID 68157806, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(S)-1-[1-(3-cyanophenyl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (200 mg, 0.55 mmol) in DCM (2 mL) was added TFA (5 mL) and the mixture was stirred at RT for 15 min. The volatiles were removed in vacuo and the resulting residue dissolved in DCM and washed with a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-7% 2M NH3/MeOH in DCM) to afford the title compound (58 mg, 40%). 1H NMR (CDCl3, 400 MHz): δ 7.93-7.66 (6H, m), 7.39-7.21 (3H, m), 7.08 (1H, d, J=7.94 Hz), 4.16-4.05 (1H, m), 1.51 (3H, d, J=7.36 Hz)

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe resulting residue dissolved in DCM
  3. washwashed with a saturated aqueous solution of NaHCO3
  4. extractionThe aqueous phase was further extracted with DCM (×3)
  5. dry with materialthe combined organic fractions were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-7% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-f01f940d3b0341c387850821d250c2ea
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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