Trifluoroacetic acid → HCID 178461903, compound

HRID 243284Notes

Reaction equation

HRID 243284 reaction equation
[N:1]1[C:9]([NH:10][C@H:11]([C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[C:16]3[CH:31]=[CH:32][CH:33]=[CH:34][C:15]=3[N:14]=2)[CH3:12])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:21]1[CH2:22][CH2:23][CH:18]([N:17]2[C:16]3[CH:31]=[CH:32][CH:33]=[CH:34][C:15]=3[N:14]=[C:13]2[C@@H:11]([NH:10][C:9]2[N:1]=[CH:2][N:3]=[C:4]3[C:8]=2[N:7]=[CH:6][NH:5]3)[CH3:12])[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178461907HCID 178461907, compound

Product 1

HCID 178461903HCID 178461903, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{2-[(S)-1-(9H-purin-6-ylamino)ethyl]benzoimidazol-1-yl}piperidine-1-carboxylic acid tertbutyl ester 112 (101 mg, 0.218 mmol) in DCM (3 mL) was added TFA (1 mL) and the mixture was stirred at RT for 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% 2M NH3/MeOH in DCM) affording 113 as a white solid (68 mg, 86%). LCMS: RT 1.65 min [M+H]+ 363.1. 1H NMR (CDCl3, 400 MHz): δ 8.34 (1H, s), 7.88 (1H, s), 7.75-7.65 (3H, m), 7.27-7.19 (3H, m), 6.01 (1H, br), 4.80-4.70 (1H, m), 3.39-3.38 (1H, m), 3.37-3.30 (1H, m), 3.19-3.09 (1H, m), 2.89-2.38 (3H, m) 1.99-1.70 (6H, m)

Workup

  1. washwas washed with MeOH
  2. washthe product eluted with 2M NH3/MeOH
  3. additionThe product containing fractions
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-97e9ce3a05ed455fa45610481aae6fb5
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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