Trifluoroacetic acid → HCID 178496642, compound

HRID 243097Notes

Reaction equation

HRID 243097 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][CH3:20])[CH2:16]2)[C:13]2[CH:21]=[C:22]([F:25])[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>[F:25][C:22]1[CH:23]=[CH:24][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([C@H:15]3[CH2:18][C@@H:17]([O:19][CH3:20])[CH2:16]3)[C:13]=2[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178496641HCID 178496641, compound

Product 1

HCID 178496642HCID 178496642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(S)-1-[6-fluoro-1-(trans-3-methoxycyclobutyl)1Hbenzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (0.125 g, 0.34 mmol) in DCM (3 mL) was added TFA (2 mL) and the mixture stirred at RT for 1.5 h. The volatiles were removed in vacuo and the resulting residue loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo. The crude material was used in the following step without further purification. Yellow oil (85 mg, 95%). LCMS (Method J): RT 1.60 min [M+H]+ 264.23. 610116410

Workup

  1. customThe volatiles were removed in vacuo
  2. washThe cartridge was washed with MeOH
  3. concentrationconcentrated in vacuo
  4. customThe crude material was used in the following step without further purification
  5. customRT 1.60 min [M+H]+ 264.23

Sources & evidence

ORD record
ord-9fcfec83fbbf4fbaa81702f0faeccfe3
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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