Trifluoroacetic acid → HCID 68157794, compound

HRID 242828Notes

Reaction equation

HRID 242828 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:13]2[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:18]1[CH2:17][CH2:16][CH:15]([N:14]2[C:13]3[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157745HCID 68157745, compound

Product 1

HCID 68157794HCID 68157794, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(S)-1-[1-(tetrahydropyran-4-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tertbutyl ester (1.80 g, 5.22 mmol) in DCM (25 mL) was added TFA (10 mL) and the mixture was stirred at RT for 1 h. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM and a saturated solution of NaHCO3. The aqueous phase was further extracted with DCM (×2) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM). The product containing fractions were concentrated in vacuo affording (S)-1-[1-(Tetrahydropyran-4-yl)-1H-benzoimidazol-2-yl]ethylamine as a light yellow solid (415 mg, 32%). LCMS: RT 0.27 min [M+Na]+ 268.1.

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue was partitioned between DCM
  3. extractionThe aqueous phase was further extracted with DCM (×2)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)
  7. additionThe product containing fractions
  8. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-f60e680acd524173b963d3f856454912
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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