Acetyl chloride → HCID 90402468, compound

HRID 2200662Notes

Reaction equation

HRID 2200662 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][C:5]([O:6][C:7]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:14]3[C:13](=[O:24])[N:12]([CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30]C4CCCCO4)[C:11](=[O:37])[N:10]([CH3:38])[C:9]=3[N:8]=2)=[CH:4][C:3]=1[C:41]([F:44])([F:43])[F:42].C(Cl)(=O)C>C(O)C>[Cl:1][C:2]1[CH:40]=[CH:39][C:5]([O:6][C:7]2[N:15]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[C:14]3[C:13](=[O:24])[N:12]([CH2:25][CH2:26][O:27][CH2:28][CH2:29][OH:30])[C:11](=[O:37])[N:10]([CH3:38])[C:9]=3[N:8]=2)=[CH:4][C:3]=1[C:41]([F:42])([F:43])[F:44]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 90402769HCID 90402769, compound

Product 1

HCID 90402468HCID 90402468, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 8-(4-chloro-3-(trifluoromethyl)phenoxy)-7-(4-chlorobenzyl)-3-methyl-1-(2-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)ethyl)-1H-purine-2,6(3H,7H)-dione (100 mg, 0.15 mmol) in ethanol (5 mL) was added acetyl chloride (0.2 mL) at 0° C. The mixture was stirred at room temperature for 1 h. The mixture was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate, filtered and concentrated to give a crude product, which was purified via preparative HPLC to give 8-(4-chloro-3-(trifluoromethyl)phenoxy)-7-(4-chlorobenzyl)-1-(2-(2-hydroxyethoxy)ethyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (37 mg, 43.1% yield) as white solid. 1H-NMR (DMSO-d6) δ 7.95(d, 1H), 7.85(d, 1H), 7.77-7.80(m, 1H), 7.44(s, 4H), 5.44(s, 2H), 4.58-4.61(m, 1H), 4.06(t, 2H), 3.59(t, 2H), 3.43-3.46(m, 4H), 3.29(s, 3). LCMS retention time 3.070 min; LCMS MH+ 573.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. customwas purified via preparative HPLC

Sources & evidence

ORD record
ord-419ba11bee5240eebbaa4521831ab3e0
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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