Trifluoroacetic acid → HCID 90402760, compound

HRID 2200734Notes

Reaction equation

HRID 2200734 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][N:8]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[C:13]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]([F:37])([F:36])[F:35])[CH:28]=3)=[N:12][C:11]=2[N:10]([CH3:38])[C:9]1=[O:39])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:14]2[C:15]3[C:16](=[O:17])[N:8]([CH2:7][C:6]([OH:40])=[O:5])[C:9](=[O:39])[N:10]([CH3:38])[C:11]=3[N:12]=[C:13]2[O:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]([F:37])([F:35])[F:36])[CH:28]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90402960HCID 90402960, compound

Product 1

HCID 90402760HCID 90402760, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 2 tert-Butyl-2-(7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8-(3-(trifluoromethoxy)phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)acetate (0.20 g, 0.34 mmol) was dissolved in DCM (4 mL) and TFA (0.26 ml, 3.4 mmol) was added. The reaction was stirred at room temperature for 15 h then evaporated under reduced pressure to give 2-(7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8-(3-(trifluoromethoxy)phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)acetic acid (0.18 g, 100% yield). LCMS retention time=3.915 minutes and 97% purity, LCMS MH+ 525. 1H NMR (DMSO-d6) δ 7.59 (t, 1H, J=8 Hz), 7.50-7.54 (m, 1H), 7.45 (d, 1H, J=8 Hz), 7.41 (s, 4H), 7.31 (d, 1H, J=8 Hz), 5.41 (s, 2H), 4.52 (s, 2H), 3.30 (s, 3H)

Workup

  1. customthen evaporated under reduced pressure

Sources & evidence

ORD record
ord-10bc11aa844a42b99d43f97f6c390128
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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