Acetohydrazide → HCID 70979115, compound

HRID 1485409Notes

Reaction equation

HRID 1485409 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:21](=[O:22])[C:13]3([CH2:15][CH:14]3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12](=S)[NH:11][C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)=[CH:4][CH:3]=1.[C:28]([NH:31][NH2:32])(=O)[CH3:29]>CCCCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:21](=[O:22])[C:13]3([CH2:15][CH:14]3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12]3=[N:32][N:31]=[C:28]([CH3:29])[N:11]3[C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 86718497HCID 86718497, compound

Product 1

HCID 70979115HCID 70979115, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of ethyl 1-(4-chlorophenyl)-2-oxo-4-thioxo-1,2,4,5-tetrahydrospiro[benzo[b][1,4]diazepine-3,1′-cyclopropane]-2′-carboxylate (70 mg, 0.17 mmol) and acetohydrazide (60 mg, 0.78 mmol) in n-BuOH (20 mL) was heated at 130° C. overnight. The solution was evaporated and purified by CombiFlash (DCM:MeOH=10:1) to afford ethyl 6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropane]-2′-carboxylate (30 mg, 41%). LRMS (M+H)+: 422 m/z. 1H NMR (300 MHz, CD3OD): δ 1.04-1.08 (t, J=7.2 Hz, 3H), 1.92-1.97 (m, 1H), 2.10-2.18 (m, 2H), 2.74 (s, 3H), 3.87-4.03 (m, 2H), 6.96-6.99 (m, 1H), 7.23-7.27 (m, 2H), 7.41-7.54 (m, 4H), 7.69-7.72 (m, 1H).

Workup

  1. customThe solution was evaporated
  2. custompurified by CombiFlash (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-f448a2658fe84c1f9d34a413d5bc91ab
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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