Hydrazinecarboxaldehyde → 1,1-Dimethylethyl 8-chloro-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-5(6H)-carboxylate

HRID 1182715Notes

Reaction equation

[CH:1]([NH:3][NH2:4])=O.[C:5]([O:9][C:10]([N:12]1[CH2:18][C:17]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:16]=2[NH:15][C:14](=S)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>O1CCOCC1>[C:5]([O:9][C:10]([N:12]1[CH2:13][C:14]2[N:15]([CH:1]=[N:3][N:4]=2)[C:16]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:17]=2[CH2:18]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

Conditions

Temperature: 90 °C

Procedure

Formylhydrazine (10.7 g, 160 mmol) was added over a period of 4 hours to a solution of 7-chloro-2-thioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester (10.0 g, 32.0 mmol) in dioxane (200 ml) at 90° C. The reaction mixture was stirred at 90° C. overnight, then evaporated. The residue was purified by chromatography (300 g silica gel, heptane: ethyl acetate, 8:2 to 0:1) to yield 7.71 g (75%) 8-chloro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester as white solid. MS m/e: 379 ([M+CH3COO−])

Workup

customevaporated
customThe residue was purified by chromatography (300 g silica gel, heptane: ethyl acetate, 8:2 to 0:1)

Sources & evidence

ORD record: ord-2aa7fd7760134816b0534edafd06971b
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664216B2

Reaction notes

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