Hydrazine → HCID 66664953, compound

HRID 2176437Notes

Reaction equation

HRID 2176437 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:32][C:13]3=[N:14][C:15]([N:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)=[CH:16][C:17](=[O:18])[N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.NN>CCO.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[S:32][C:13]3=[N:14][C:15]([N:19]4[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:23][CH2:24]4)=[CH:16][C:17](=[O:18])[N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 9321Hydrazine2×HCID 66668749HCID 66668749, compound

Product 1

HCID 66664953HCID 66664953, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 4-(2-(3-nitrophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (769 mg, 1.677 mmol) in EtOH (12 ml) at room temperature is added Raney® 2400 nickel (98 mg, 1.677 mmol) followed by hydrazine (0.526 ml, 16.77 mmol) dropwise and the mixture is stirred at room temperature for 4 hours. The reaction is monitored by TLC and LMCMS and additional nickel and hydrazine is added until completion. The mixture is filtered over celite and concentrated in vacuo to give crude tert-butyl 4-(2-(3-aminophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (443 mg, 1.034 mmol, 61.6% yield) as a tan solid.

Workup

  1. additionis added until completion
  2. filtrationThe mixture is filtered over celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f04a519e216468da89960037f9314d9
Source dataset
uspto-grants-2015_06
Patent number
US09066948B2

Reaction notes

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