Isopropylamine → HCID 90402588, compound

HRID 2200695Notes

Reaction equation

HRID 2200695 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12](=[O:17])[N:11]([CH3:18])[C:10]=3[N:9]=[C:8]2[S:19](Cl)(=[O:21])=[O:20])=[CH:4][CH:3]=1.[CH:25]([NH2:28])([CH3:27])[CH3:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12](=[O:17])[N:11]([CH3:18])[C:10]=3[N:9]=[C:8]2[S:19]([NH:28][CH:25]([CH3:27])[CH3:26])(=[O:21])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 90402802HCID 90402802, compound2×

Product 1

HCID 90402588HCID 90402588, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-sulfonyl chloride (115 mg, 0.295 mmol, intermediate 64) in DCM (5 mL) was added isopropylamine (17.4 mg, 0.59 mmol) followed by TEA (60 mg, 0.59 mmol) at 0° C. and the mixture was stirred at room temperature for 1 h. The mixture was diluted with DCM and washed brine. The organic phase was dried and concentrated to give a crude product, which was purified by silica gel chromatography eluting with DCM/methanol (50:1) to give 7-(4-chlorobenzyl)-N-isopropyl-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-sulfonamide (59 mg, 48.6% yield) as yellow syrup. LCMS retention time 1.436 min; LCMS MH+ 412.

Workup

  1. washwashed brine
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customto give a crude product, which
  5. customwas purified by silica gel chromatography
  6. washeluting with DCM/methanol (50:1)

Sources & evidence

ORD record
ord-1ee44456ea3243e7a36ea418017ee478
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

Loading…