Hydrazine hydrate (1:1) → 5-(4-bromophenyl)-3-(1-hydroxymethyl-1-methylethyl)-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazole-6-one

HRID 2037183Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[C:11]([C:21](=O)[C:22]([CH3:32])([CH3:31])[CH2:23][O:24]C3CCCCO3)=[C:10](O)[C:9]2=[O:35])=[CH:4][CH:3]=1.O.[NH2:37][NH2:38].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[C:11]3[C:21]([C:22]([CH2:23][OH:24])([CH3:32])[CH3:31])=[N:38][NH:37][C:10]=3[C:9]2=[O:35])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 1-(4-bromophenyl)-4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-one (1.51 g, 2.77 mmol), hydrazine hydrate (0.204 mL, 4.16 mmol) and acetic acid (3 mL) was stirred at 95° C. for 2 hours. After the reaction was completed, saturated sodium bicarbonate solution (150 mL) was poured into the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was triturated with ethyl acetate to give 5-(4-bromophenyl)-3-(1-hydroxymethyl-1-methylethyl)-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazole-6-one (1.02 g, yield: 81%) as colorless solid.

Workup

extractionthe resulting mixture was extracted with ethyl acetate
washThe extract was washed with saturated sodium bicarbonate solution
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated in vacuo
customThe resulting residue was triturated with ethyl acetate

Sources & evidence

ORD record: ord-2194db0e45f146c7b22fc0d699b4f4a6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575197B2

Reaction notes

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