Trifluoroacetic acid → Trifluoroacetate

HRID 736663Notes

Reaction equation

HRID 736663 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([S:26][C:27]1[C:35]([Br:36])=[CH:34][C:30]3[O:31][CH2:32][O:33][C:29]=3[CH:28]=1)[N:6]2[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>C(Cl)Cl>[Br:36][C:35]1[C:27]([S:26][C:5]2[N:6]([CH2:11][CH2:12][CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[C:7]3[C:3]([N:4]=2)=[C:2]([NH2:1])[N:10]=[CH:9][N:8]=3)=[CH:28][C:29]2[O:33][CH2:32][O:31][C:30]=2[CH:34]=1.[F:37][C:38]([F:43])([F:42])[C:39]([O-:41])=[O:40]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57850223HCID 57850223, compound

Product 2

HCID 84468TrifluoroacetateHCID 57850593HCID 57850593, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-Butyl 4-(2-{6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)thio]-9H-purin-9-yl}ethyl)piperidine-1-carboxylate (0.030 g) in DCM (10 mL) was added trifluoroacetic acid (5 mL) at room temperature and stirring was continued at rt for 1-16 h. The solvent and the excess trifluoroacetic acid was evaporated to dryness. The oily residue was co-evaporated with toluene (3×5 mL) to afford title product as a trifluoroacetate salt. 1H NMR (DMSO-d6) δ 8.21 (s, 1H), 7.40 (s, 1H), 6.85 (s, 1H), 6.10 (s, 2H), 4.19 (t, J=7.6 Hz, 2H), 3.25-3.20 (m, 2H), 2.80-2.75 (m, 2H), 1.88-1.85 (m, 2H), 1.68-1.62 (m, 2H), 1.50-1.42 (M, 1H), 1.30-1.24 (m, 2H); LC-MS [M+H]+ 477.1

Workup

  1. customThe solvent and the excess trifluoroacetic acid was evaporated to dryness

Sources & evidence

ORD record
ord-71a4791716f84ceba84b60a8635494a1
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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