Acetohydrazide → HCID 70978881, compound

HRID 1485400Notes

Reaction equation

HRID 1485400 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[CH2:13][C:12](=S)[NH:11][C:10]2[CH:17]=[CH:18][CH:19]=[CH:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([NH:24][NH2:25])(=O)[CH3:22]>C(O)CCC>[CH2:1]([N:8]1[C:14](=[O:15])[CH2:13][C:12]2=[N:25][N:24]=[C:21]([CH3:22])[N:11]2[C:10]2[CH:17]=[CH:18][CH:19]=[CH:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 86718495HCID 86718495, compound

Product 1

HCID 70978881HCID 70978881, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 1-benzyl-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (50 mg, 0.18 mmol) and acetohydrazide (40 mg, 0.53 mmol) in 20 mL of n-butanol was heated to reflux, and stirred for 24 h under N2 atmosphere. The solvent was evaporated in vacuo and the residue was purified by prep-TLC (DCM:MeOH=25:1) to give 6-benzyl-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (20 mg, 38%). 1H NMR (300 MHz, CD3OD): δ 2.36 (s, 3H), 3.77 (d, J=14.1 Hz, 1H), 3.98 (d, J=14.1 Hz, 1H), 4.69 (d, J=15 Hz, 1H), 5.64 (d, J=15 Hz, 1H), 6.77-6.80 (m, 2H), 7.13-7.16 (m, 3H), 7.49-7.62 (m, 3H), 7.82-7.85 (m, 1H). LRMS (M+H)+: 304 m/z.

Workup

  1. temperatureto reflux
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by prep-TLC (DCM:MeOH=25:1)

Sources & evidence

ORD record
ord-6d5fff4f1b784985abe5742858b8c66f
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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