Hydrazine hydrate (1:1) → HCID 178436769, compound

HRID 1865137Notes

Reaction equation

C[N:2]([CH:4]=[N:5][C:6]([C:8]1[N:9]([CH3:31])[C:10]([CH2:29][CH3:30])=[C:11]([C:27]#[N:28])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:15][CH:14]=1)=O)C.O.[NH2:33]N>C(O)(=O)C>[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:16]1[CH:17]=[CH:18][C:13]([C:12]2[C:11]([C:27]#[N:28])=[C:10]([CH2:29][CH3:30])[N:9]([CH3:31])[C:8]=2[C:6]2[NH:5][CH:4]=[N:2][N:33]=2)=[CH:14][CH:15]=1)#[N:26]

Participants

Conditions

Temperature: 90 °C

Procedure

Dissolve 4-cyano-3-(2′-cyano-biphenyl-4-yl)-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid dimethylaminomethyleneamide (183 mg, 0.45 mmol, prepared in preparation 47) in 2 mL of glacial acetic acid, add hydrazine monohydrate (0.70 mmol) and heat to 90° C. under nitrogen. After 90 minutes cool the reaction slightly, pour into 50 mL of ice-water and stir for twenty minutes. Filter off the resulting solid and rinse with 10 mL of water. Vacuum-dry overnight to give the title compound (66 mg, 39%). MS(ES+, m/e)=379 (M++1).

Workup

temperatureAfter 90 minutes cool
customthe reaction slightly
filtrationFilter off the resulting solid
washrinse with 10 mL of water
customVacuum-dry overnight

Sources & evidence

ORD record: ord-5ddd5b3de954472d8b5c5bc8fa1a26b4
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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