HCID 15542772, compound → HCID 15542773, compound

HRID 1699513Notes

Reaction equation

[O:1]=[S:2]1(=[O:16])[C:7]2=[CH:8][CH:9]=[CH:10][C:11]3=[CH:12][CH:13]=[CH:14][C:5](=[C:6]23)[C:4](=O)[NH:3]1>O1CCCC1>[S:2]1(=[O:1])(=[O:16])[C:7]2=[CH:8][CH:9]=[CH:10][C:11]3=[CH:12][CH:13]=[CH:14][C:5](=[C:6]23)[CH2:4][NH:3]1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 1,1-dioxo-2,3-dihydro-naphtho[1,8-de][1,2]thiazin-3-one (137 mg, 0.587 mmol) in anhydrous tetrahydrofuran (2 mL) was treated with a 1.0M solution of borane-tetrahydrofuran complex in tetrahydrofuran (1.17 mL, 1.17 mmol). The resulting solution was heated at 65° C. for 5 hours. The reaction mixture was quenched with methanol (5 mL) and evaporated under vacuum. The residue was purified by preparative layer chromatography on two 1 mm×20 cm×20 cm silica gel GF plates, developing with 7:3 ethyl acetate-hexanes, to afford the title compound (78 mg, 61% yield).

Workup

customThe reaction mixture was quenched with methanol (5 mL)
customevaporated under vacuum
customThe residue was purified by preparative layer chromatography on two 1 mm×20 cm×20 cm silica gel GF plates

Sources & evidence

ORD record: ord-bfe6e64d1c004d39a3364706c3fb1277
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346526B1

Reaction notes

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