Hydrazine → 9-Amino-3-ethyl-3H-pyrazolo[4',3':5,6]pyrido[3,4-d]pyridazin-6(7H)-one

HRID 429046Notes

Reaction equation

[C:1]([C:3]1[C:8]([C:9](OCC)=[O:10])=[CH:7][N:6]=[C:5]2[N:14]([CH2:17][CH3:18])[N:15]=[CH:16][C:4]=12)#[N:2].[NH2:19][NH2:20]>C(O)C>[NH2:2][C:1]1[C:3]2[C:4]3[CH:16]=[N:15][N:14]([CH2:17][CH3:18])[C:5]=3[N:6]=[CH:7][C:8]=2[C:9](=[O:10])[NH:19][N:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 4-cyano-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester (10.0 g, 40.1 mmol) in ethanol (100 mL) was added anhydrous hydrazine (5 eq). This suspension was then heated at 80° C. until starting material was consumed. The reaction was allowed to cool to rt and diluted with water (200 mL). The resulting solid was filtered and washed thoroughly with water until the filtrate was colorless. The solid was dried under vacuum to afford the title compound as a yellow solid (5.5 g, 60%). This material was >90% pure as judged by HPLC and was used directly.

Workup

customwas consumed
temperatureto cool to rt
additiondiluted with water (200 mL)
filtrationThe resulting solid was filtered
washwashed thoroughly with water until the filtrate
customThe solid was dried under vacuum

Sources & evidence

ORD record: ord-5d62c2453b7c40c59a56c8547fdf3f3a
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06316438B1

Reaction notes

Loading…