HCID 68159059, compound → HCID 68157047, compound

HRID 243261Notes

Reaction equation

HRID 243261 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH3:15])[C:13]2[C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[C:17]([F:20])[CH:18]=[CH:19][C:12]=2[N:11]=1)[CH3:9])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:20][C:17]1[CH:18]=[CH:19][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([CH3:15])[C:13]=2[C:16]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

4

Reactant 1

HCID 68159059HCID 68159059, compound

Product 1

HCID 68157047HCID 68157047, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[(S)-1-(6-Fluoro-1-methyl-7-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (0.3 g, 0.81 mmol) was dissolved in 20% TFA in DCM (10 mL). The resulting solution was stirred for 1 h then the mixture was passed through an SCX column. The column was washed with DCM, MeOH and the product was eluted with 2M NH3 in MeOH. The product fractions were concentrated to give a yellow solid (0.2 g, 92%). LCMS (Method J): RT 1.39 min [M+H]+ 271

Workup

  1. washThe column was washed with DCM, MeOH
  2. washthe product was eluted with 2M NH3 in MeOH
  3. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-4bd409ceed3343ddbea1ec984bb6c006
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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