Semicarbazide → [(E)-1-[3-[(5,7-difluoroquinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]urea

HRID 456110Notes

Reaction equation

[F:1][C:2]1[C:11]([CH2:12][C:13]2[N:17]3[N:18]=[C:19]([C:22](=O)[CH3:23])[CH:20]=[CH:21][C:16]3=[N:15][N:14]=2)=[C:10]([F:25])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[NH2:26][NH:27][C:28]([NH2:30])=[O:29].C(=O)(O)[O-].[Na+]>CO>[F:1][C:2]1[C:11]([CH2:12][C:13]2[N:17]3[N:18]=[C:19](/[C:22](=[N:26]/[NH:27][C:28]([NH2:30])=[O:29])/[CH3:23])[CH:20]=[CH:21][C:16]3=[N:15][N:14]=2)=[C:10]([F:25])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 1-[3-(5,7-difluoro-quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-ethanone (38 mg, 0.112 mmol), semicarbazide (37.5 mg, 0.336 mmol) and sodium bicarbonate (40 mg, 0.67 mmol) in methanol (3 mL) was stirred at 40° C. for 20 h. LC/MS showed the reaction was complete, and the suspension was filtered. The filtrate cake was washed successively with cold water and methanol, and then dried to afford 36.3 mg (82% yield) of the title compound as white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.85 (s, 1H), 8.99 (dd, 1H), 8.49 (d, 1H), 8.35 (d, 1H), 8.18 (d, 1H), 7.73 (d, 1H), 7.62 (dd, 1H), 6.82 (s br, 2H), 4.75 (s, 2H), 2.19 (s, 3H). LCMS (method A): [MH]+=397, tR=4.43 min.

Workup

filtrationthe suspension was filtered
washThe filtrate cake was washed successively with cold water and methanol
customdried

Sources & evidence

ORD record: ord-f9c9b81e6f4142699d68436767792d15
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497368B2

Reaction notes

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