Trifluoroacetic acid → HCID 57850178, compound

HRID 736671Notes

Reaction equation

HRID 736671 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-7262b351f5f040d49169296bfc4cb248
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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