4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → HCID 71519591, compound

HRID 1465790Notes

Reaction equation

HRID 1465790 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[S:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:11]=2[N:12]=1.[CH3:19][C:20]1[C:28]2[CH2:27][O:26][C:25](=[O:29])[C:24]=2[CH:23]=[CH:22][C:21]=1[C@@H:30]1[CH2:32][O:31]1>CCO>[OH:31][C@H:30]([C:21]1[CH:22]=[CH:23][C:24]2[C:25](=[O:29])[O:26][CH2:27][C:28]=2[C:20]=1[CH3:19])[CH2:32][N:6]1[CH2:5][CH2:4][N:3]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:11]=3[N:12]=2)[C:2](=[O:1])[CH2:7]1

Participants

4

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 89526278HCID 89526278, compound

Product 1

HCID 71519591HCID 71519591, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 2-(2-Oxopiperazin-1-yl)-1,3-benzothiazole-5-carbonitrile [I-8] (25 mg, 0.10 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (37 mg, 0.19 mmol) in EtOH (2 mL) in a 5 mL microwave tube was heated to 145° C. for 1.5 hours. LC showed formation of the title product, which was purified by silica gel flash chromatography. LC-MS (IE, m/z): 449 [M+1]+.

Sources & evidence

ORD record
ord-2d56287bb28346009ff6ae50aa7e7bab
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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