Trifluoroacetic acid → HCID 57850178, compound

HRID 445095Notes

Reaction equation

HRID 445095 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH3:40])[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][N:19]2[C:27]([S:28][C:29]3[C:37]([Br:38])=[CH:36][C:32]4[O:33][CH2:34][O:35][C:31]=4[CH:30]=3)=[N:26][C:25]3[C:20]2=[N:21][CH:22]=[N:23][C:24]=3[NH2:39])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH3:40])[C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][N:19]2[C:27]([S:28][C:29]3[C:37]([Br:38])=[CH:36][C:32]4[O:33][CH2:34][O:35][C:31]=4[CH:30]=3)=[N:26][C:25]3[C:20]2=[N:21][CH:22]=[N:23][C:24]=3[NH2:39])[CH2:15][CH2:16]1)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57850041HCID 57850041, compound

Product 1

HCID 57850178HCID 57850178, compoundYield 130.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-2-(4-{2-[6-Amino-8-(6-bromo-benzo[1,3]dioxol-5-ylsulfanyl)-purin-9-yl]-ethyl}-piperidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (0.014 g, 0.021 mmol) in DCM (3 mL) was added drop wise TFA (100 μL) and the resulting mixture was stirred for overnight at room temperature. After concentration under reduced pressure, the residual TFA was removed to afford a title product (0.015 g) as a TFA salt. 1H NMR (CD3OD) δ 8.34 (s, 1H), 7.28 (s, 1H), 7.23 (s, 1H), 6.09 (s, 2H), 4.54-4.44 (m, 2H), 4.39 (t, J=7.42 Hz, 2H), 3.85 (broad d, J=13.2 Hz, 1H), 3.19-3.08 (m, 1H), 2.75-2.63 (m, 1H), 2.00-1.80 (m, 4H), 1.70-1.58 (m, 1H), 1.44 (dd, J=14.8, 7.0 Hz, 3H), 1.35-1.13 (m, 2H); LC-MS [M+H]+ 548.2

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residual TFA was removed

Sources & evidence

ORD record
ord-67ea6d4cb0db4464b4f335dfac6cf1c7
Source dataset
uspto-grants-2013_07
Patent number
US08476285B2

Reaction notes

Loading…