m-Chloroperbenzoic acid → HCID 66758275, compound

HRID 1507796Notes

Reaction equation

HRID 1507796 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:29])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:15][CH2:14]2)[C:5]2[N:10]=[C:9]([S:11][CH3:12])[S:8][C:6]=2[N:7]=1.C1C=C(Cl)C=C(C(OO)=[O:38])C=1>ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:29])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:15][CH2:14]2)[C:5]2[N:10]=[C:9]([S:11]([CH3:12])=[O:38])[S:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 46916620HCID 46916620, compound

Product 1

HCID 66758275HCID 66758275, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cooled suspension of 5-amino-7-[4-(4-chlorophenoxyacetyl)piperazin-1-yl]-2-methylthio-thiazolo[5,4-d]pyrimidine (90 mg, 0.2 mmol) in dichloromethane (5 ml) was added mCPBA (125 mg, 0.5 mmol). The resulting mixture was stirred at 0° C. for 2 h. The solvents were evaporated in vacuo and the crude residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1/80), yielding the pure title compound (65 mg, 70%).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe crude residue was purified by flash chromatography on silica
  3. additiona mixture of methanol and dichloromethane (in a ratio of 1/80),

Sources & evidence

ORD record
ord-ccfcfa0f97e446fbbf2f298a6a6e143f
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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