HCID 68157672, compound → HCID 68157272, compound

HRID 243169Notes

Reaction equation

HRID 243169 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)[C:13]2[CH:23]=[C:24]([F:27])[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>[F:22][C:17]1[CH:16]=[C:15]([N:14]2[C:13]3[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:12]=3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH:20]=[C:19]([F:21])[CH:18]=1

Participants

4

Reactant 1

HCID 68157672HCID 68157672, compound

Product 1

HCID 68157272HCID 68157272, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of {(S)-1-[1-(3,5-difluorophenyl)-6-fluoro-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (668 mg, 1.7 mmol) in TFA (4 mL) and DCM (12 mL) was stirred for 1 h at RT. The reaction solution was 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 to afford the title compound as a pale yellow oil (497 mg, 99%). Marfey's test: 97% de. LCMS (Method C): RT 1.96 min [M+H]+ 292. 1H NMR (CDCl3, 400 MHz): δ 7.70 (1H, dd, J=9.0, 5.0 Hz), 7.08-7.00 (2H, m), 6.97-6.93 (2H, m), 6.80 (1H, dd, J=8.0, 2.5 Hz), 6.19 (2H, bs), 4.51 (1H, q, 7.0 Hz), 1.55 (3H, d, J=7.0 Hz).

Workup

  1. washThe cartridge was washed with MeOH
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c2973dcb0a9402b9da9d88943ab3799
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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