HCID 68157902, compound → HCID 68156978, compound

HRID 243174Notes

Reaction equation

HRID 243174 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]2[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[C:20]([F:23])[CH:21]=[CH:22][C:12]=2[N:11]=1)[CH3:9])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:23][C:20]1[CH:21]=[CH:22][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]=2[C:19]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

4

Reactant 1

HCID 68157902HCID 68157902, compound

Product 1

HCID 68156978HCID 68156978, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of {(S)-1-[6-fluoro-1-(2-methoxyethyl)-7-pyridin-2-yl-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (231 mg, 0.56 mmol) in TFA (2 mL) and DCM (6 mL) was stirred for 45 min at RT. The reaction mixture 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 (179 mg, 99%). Marfey's test: >99% de. LCMS (Method C): RT 1.76 min [M+H]+ 315. 1H NMR (CDCl3, 400 MHz): δ 8.75 (1H, ddd, J=5.0, 2.0, 1.0 Hz), 7.84 (1H, ddd, J=7.5, 7.5, 2.0 Hz), 7.73 (1H, dd, J=9.0, 5.0 Hz), 7.60-7.57 (1H, m), 7.38 (1H, ddd, J=7.5, 5.0, 1.0 Hz), 7.09 (1H, dd, J=10.0, 9.0 Hz), 4.33 (1H, q, J=6.5 Hz), 4.12 (1H, ddd, J=15.5, 5.5, 4.5 Hz), 4.02 (1H, ddd, J=15.5, 7.0, 5.0 Hz), 3.12-3.01 (2H, m), 3.06 (3H, m), 2.00 (2H, bs), 1.59 (3H, d, J=6.5 Hz).

Workup

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

Sources & evidence

ORD record
ord-496d018764254cce987b1e06132c9211
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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