Trifluoroacetic acid → HCID 57565640, compound

HRID 1727029Notes

Reaction equation

HRID 1727029 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH3:16])[C:10](=[O:17])[N:9]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[C:8]=2[N:7]=[C:6]1[N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH3:16])[C:10](=[O:17])[N:9]([CH2:18][C:19]([OH:21])=[O:20])[C:8]=2[N:7]=[C:6]1[N:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57565594HCID 57565594, compound

Product 1

HCID 57565640HCID 57565640, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl [7-(2-chloro-6-fluorobenzyl)-1-ethyl-2,6-dioxo-8-piperidin-1-yl-1,2,6,7-tetrahydro-3H-purin-3-yl]acetate (24 mg, 0.046 mmol) in 230 μL CH2Cl2 was treated with 230 μL TFA. The reaction was stirred at room temperature for 1 hr and then the solvent was removed by reduced pressure. The crude product was filtered through a silica plug and rinsed with 20% MeOH/EtOAc. The solvent was removed affording the title compound (19 mg, 90% yield) as a white solid: 1H NMR (CDCl3, 400 MHz) 7.22-7.16 (m, 1H), 7.14-7.10 (m, 1H), 6.98-6.91 (m, 1H), 5.51 (s, 2H), 4.80 (s, 2H), 3.95 (q, 2H, J=7.0 Hz), 3.11-3.01 (m, 4H), 1.54-1.41 (m, 6H), 1.12 (t, 3H, J=7.0 Hz); MS (ESP+) m/e 464 (MH+).

Workup

  1. customthe solvent was removed by reduced pressure
  2. filtrationThe crude product was filtered through a silica plug
  3. washrinsed with 20% MeOH/EtOAc
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-abaec6f409f54a4b9ccd888a5dc1957b
Source dataset
uspto-grants-2009_02
Patent number
US07495004B2

Reaction notes

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