Trifluoroacetic acid → HCID 90403561, compound

HRID 2200654Notes

Reaction equation

HRID 2200654 reaction equation
C([NH:5][S:6]([CH2:9][N:10]1[C:18](=[O:19])[C:17]2[N:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[C:15]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:39])([F:38])[F:37])[CH:30]=3)=[N:14][C:13]=2[N:12]([CH3:40])[C:11]1=[O:41])(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:16]2[C:17]3[C:18](=[O:19])[N:10]([CH2:9][S:6]([NH2:5])(=[O:8])=[O:7])[C:11](=[O:41])[N:12]([CH3:40])[C:13]=3[N:14]=[C:15]2[O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:37])([F:39])[F:38])[CH:30]=2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90403134HCID 90403134, compound

Product 1

HCID 90403561HCID 90403561, compoundYield 72.4%

Procedure

A solution of N-tert-butyl-1-(7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8-(3-(trifluoromethoxy)phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)methanesulfonamide (120 mg, 0.195 mmol, example 71) in TFA (2 ml, 26.9 mmol) was stirred at 50° C. for 16 h. The mixture was concentrated and then purified by silica gel chromatography eluting with DCM/methanol (40:1) to give (7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8-(3-(trifluoromethoxy)phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)methanesulfonamide (79 mg, 72.4% yield) as white solid. 1H-NMR (DMSO-d6) δ 7.65-7.61(t, 1H), 7.49(s, 1H), 7.47-7.41(m, 6H), 7.36-7.35(d, 1H), 7.05(s, 2H), 5.45(s, 2H), 5.23(s, 2H), 3.31(s, 3H). LCMS retention time 3.004 min; LCMS MH+ 560.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel chromatography
  3. washeluting with DCM/methanol (40:1)

Sources & evidence

ORD record
ord-c6ec551589e44d49b33d51d3bf0f2814
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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