HCID 68157046, compound → HCID 68157615, compound

HRID 243380Notes

Reaction equation

HRID 243380 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]=2)[C:13]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:12]=2[N:11]=1)[CH3:9])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:26][C:23]1[CH:24]=[CH:25][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]=3)[C:13]=2[CH:22]=1

Participants

4

Reactant 1

HCID 68157046HCID 68157046, compound

Product 1

HCID 68157615HCID 68157615, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of {(S)-1-[6-fluoro-1-(5-fluoropyridin-2-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (33 mg, 0.09 mmol) in DCM (1 mL) and TFA (0.5 mL) was stirred at RT for 2 h. The crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge and washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo to afford (S)-1-[6-fluoro-1-(5-fluoropyridin-2-yl)-1H-benzoimidazol-2-yl]ethylamine as a yellow oil (19 mg, 79%). LCMS (Method C): RT 0.27 and 1.84 min [M+H]+ 275.2.

Workup

  1. customThe crude reaction mixture
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65edcd8ec4e24b1a8e19adca3e55ac4f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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