Acetohydrazide → HCID 70979775, compound

HRID 1485471Notes

Reaction equation

HRID 1485471 reaction equation
[F:1][C:2]1[C:7]2[NH:8][C:9](=S)[CH2:10][CH2:11][NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:14]([NH:17][NH2:18])(=O)[CH3:15]>C(O)CCC>[F:1][C:2]1[C:7]2[N:8]3[C:14]([CH3:15])=[N:17][N:18]=[C:9]3[CH2:10][CH2:11][NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 86718508HCID 86718508, compound

Product 1

HCID 70979775HCID 70979775, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A disposable tube was charged with 9-fluoro-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione (40 mg, 0.204 mmol) and a stirbar. nBuOH (5 mL) was added, followed by acetohydrazide (30.2 mg, 0.408 mmol), and the solution was stirred at 130° C. overnight. The solution was concentrated with celite and purified by silica gel chromatography (eluting with methylene chloride/methanol/1% ammonium hydroxide) to yield 10-fluoro-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine as an off-white amorphous solid (0.022 g, 0.101 mmol, 50%).

Workup

  1. concentrationThe solution was concentrated with celite
  2. custompurified by silica gel chromatography (eluting with methylene chloride/methanol/1% ammonium hydroxide)

Sources & evidence

ORD record
ord-42966bc7cad542a28f7e1a7ee91eb384
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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