Dimethyl Sulfoxide → HCID 68777580, compound

HRID 1253889Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:12]=2[NH:11][C:10](=S)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:21]([NH:23][NH2:24])=O.CS(C)=O>C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]2[N:11]([CH:21]=[N:23][N:24]=2)[C:12]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:13]=2[CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 8-fluoro-2-thioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester (2.36 g, 7.97 mmol) in dry benzene (25 mL), was added formic acid hydrazide dissolved in 5 mL of dry DMSO (1.43 g, 23.91 mmol) at room temperature. The reaction mixture was heated at 80° C., using Dean-Stark apparatus for 18 h. After the completion of the reaction, as confirmed by TLC, distilled water (40 mL) was added and the crude compound was extracted with diethyl ether (3×40 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford the crude compound which, was purified by column chromatography [silica gel, 1.5:8.5 Acetone:Pet. ether] to afford 9-fluoro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester, (1.455 g, 60%) as a white solid.

Workup

customfor 18 h
customAfter the completion of the reaction
distillationdistilled water (40 mL)
additionwas added
extractionthe crude compound was extracted with diethyl ether (3×40 mL)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated in vacuo
customto afford the crude compound which
customwas purified by column chromatography [silica gel, 1.5:8.5 Acetone:Pet. ether]

Sources & evidence

ORD record: ord-20ce759109b641ffac828518a94a5799
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455479B2

Reaction notes

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