HCID 90402884, compound → HCID 90402378, compound

HRID 2200697Notes

Reaction equation

HRID 2200697 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][O:20]C4CCCCO4)[C:12](=[O:27])[N:11]([CH3:28])[C:10]=3[N:9]=[C:8]2[S:29]([NH:32][CH:33]([CH3:35])[CH3:34])(=[O:31])=[O:30])=[CH:4][CH:3]=1>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:27])[N:11]([CH3:28])[C:10]=3[N:9]=[C:8]2[S:29]([NH:32][CH:33]([CH3:34])[CH3:35])(=[O:30])=[O:31])=[CH:36][CH:37]=1

Participants

3

Reactant 1

HCID 90402884HCID 90402884, compound

Product 1

HCID 90402378HCID 90402378, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 7-(4-chlorobenzyl)-N-isopropyl-3-methyl-2,6-dioxo-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-2,3,6,7-tetrahydro-1H-purine-8-sulfonamide (61 mg, 0.11 mmol) in 1 mM ethanolic HCl (1 mL, 1 mmol/L) was stirred at room temperature for 30 min. The mixture was concentrated and purified by preparative HPLC to give 7-(4-chlorobenzyl)-1-(3-hydroxypropyl)-N-isopropyl-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-sulfonamide (17.9 mg, 34.6% yield) as white solid. 1H-NMR (CD3OD) δ 7.31-7.38(m, 4H), 5.89(s, 2H), 4.06-4.10 (t, 2H), 3.58-3.63 (m, 3H), 3.56 (s, 3H), 1.83-1.87 (m, 2H), 1.19-1.21 (d, 6H). LCMS retention time 2.315 min; LCMS MH+ 470.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d4f5d5f7df934b9fb93b0a4514bed2a6
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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