Trifluoroacetic acid → HCID 68156981, compound

HRID 243365Notes

Reaction equation

HRID 243365 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[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:21]1[CH:20]=[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:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157593HCID 68157593, compound

Product 1

HCID 68156981HCID 68156981, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(S)-1-[3-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethyl}carbamic acid tert-butyl ester (35 mg, 0.09 mmol) in DCM (1 mL) was added TFA (1 mL) and the 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-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethylamine as an orange oil (23 mg).

Workup

  1. washwashed with MeOH
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fff9ef130b484143bde735d6cb875de8
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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