Trifluoroacetic acid → HCID 178461909, compound

HRID 242823Notes

Reaction equation

HRID 242823 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[C@@H:23]([NH:25][C:26]2[N:34]=[CH:33][N:32]=[C:31]3[C:27]=2[N:28]=[CH:29][N:30]3C2CCCCO2)[CH3:24])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[C@@H:23]([NH:25][C:26]2[N:34]=[CH:33][N:32]=[C:31]3[C:27]=2[N:28]=[CH:29][NH:30]3)[CH3:24])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157943(R)-3-(2-{(S)-1-[9-(Tetrahydropyran-2-yl)-9H-purin-6-ylamino]ethyl}benzoimidazol-1-yl)piperidine-1-carboxylic acid tertbutyl ester

Product 1

HCID 178461909HCID 178461909, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-(2-{(S)-1-[9-(tetrahydropyran-2-yl)-9H-purin-6-ylamino]ethyl}benzoimidazol-1-yl)piperidine-1-carboxylic acid tertbutyl ester (2.27 g, 4.15 mmol) in DCM (25 mL) was added TFA (15 mL) and the mixture was stirred at RT for 1 h. Volatiles were removed under reduced pressure and the resulting residue was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with a 1:1 mixture MeOH:DCM and the product was eluted with 2M NH3/MeOH (100 mL) in DCM (150 mL). The product containing fractions were combined and concentrated in vacuo affording [(S)-1-((R)-1-Piperidin-3-yl-1H-benzoimidazol-2-yl)ethyl]-(9H-purin-6-yl)amine as a pale yellow solid (1.53 g, quantitative). LCMS: RT 1.63 min [M+H]+ 363.2.

Workup

  1. customVolatiles were removed under reduced pressure
  2. washThe cartridge was washed with a 1:1 mixture MeOH
  3. washDCM and the product was eluted with 2M NH3/MeOH (100 mL) in DCM (150 mL)
  4. additionThe product containing fractions
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17b7c94c3538411997b24bb6fe00a2fc
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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