Trifluoroacetic acid → HCID 68158171, compound

HRID 243366Notes

Reaction equation

HRID 243366 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:18]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([N:18]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157293HCID 68157293, compound

Product 1

HCID 68158171HCID 68158171, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of {(S)-1-[3-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethyl}carbamic acid tert-butyl ester (99 mg, 0.27 mmol) in DCM (1 mL) was added TFA (1 mL) and the reaction mixture was stirred at RT for 3 h. The crude 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-[3-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethylamine as an orange oil (71 mg).

Workup

  1. washwashed with MeOH
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef888e5ebefa4e539a43a781c7c55eb2
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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