Trifluoroacetic acid → HCID 57850328, compound

HRID 445069Notes

Reaction equation

HRID 445069 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[C:24]([S:25][C:26]3[C:34]([Br:35])=[CH:33][C:29]4[O:30][CH2:31][O:32][C:28]=4[CH:27]=3)=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[NH2:36])=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl.C1(C)C=CC=CC=1>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[C:24]([S:25][C:26]3[C:34]([Br:35])=[CH:33][C:29]4[O:30][CH2:31][O:32][C:28]=4[CH:27]=3)=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[NH2:36])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57850781HCID 57850781, compound

Product 1

HCID 57850328HCID 57850328, compoundYield 154.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-{2-[6-Amino-8-(6-bromo-benzo[1,3]dioxol-5-ylsulfanyl)purin-9-yl]-ethyl}-phenyl)-carbamic acid tert-butyl ester (0.03 g, 0.04 mmol) in dichloromethane (4.3 mL) was added TFA (0.02 mL, 0.22 mmol) and the reaction mixture was stirred at rt overnight. At the end of this period, reaction was diluted with 100 mL of toluene and then concentrated under reduced pressure. This process was repeated 3 more times to yield the title product (0.03 g, 95%) as TFA salt. 1H NMR (DMSO-d6) δ 8.19 (s, 1H), 7.24 (s, 1H), 7.19-7.02 (m, 4H), 7.00 (s, 1H), 6.13 (s, 2H), 4.45 (t, J=6.8 Hz, 2H), 3.18 (t, J=6.8 Hz, 2H); LC-MS [M+H]+ 486.3.

Workup

  1. customAt the end of this period, reaction
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15ad712b7ef9441ca71210eb692eeaeb
Source dataset
uspto-grants-2013_07
Patent number
US08476285B2

Reaction notes

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