2-(4-Morpholinyl)acetohydrazide → HCID 71699898, compound

HRID 456101Notes

Reaction equation

[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9]([C:12](=O)[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[O:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]([NH:35][NH2:36])=[O:34])[CH2:28][CH2:27]1>CO>[F:25][C:2]([F:1])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9](/[C:12](=[N:36]/[NH:35][C:33](=[O:34])[CH2:32][N:29]3[CH2:30][CH2:31][O:26][CH2:27][CH2:28]3)/[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1

Participants

Conditions

Temperature: 45 °C

Procedure

1-(3-(difluoro(quinolin-6-yl)methyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (25 mg, 0.074 mmol) and 2-morpholinoacetohydrazide (12 mg, 0.075 mmol) were dissolved in MeOH and the pH of the reaction solution was adjusted to 5. The solution was then stirred at 45° C. for 3 hours. Solvent was evaporated and the crude product was purified on HPLC (neutralized to free base) to give the title compound as a white solid (18 mg, 50%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.02 (s, 1H), 8.55 (d, 1H), 8.43 (d, 2H), 8.17 (d, 1H), 8.01 (m, 2H), 7.65 (d, 1H), 3.59 (m, 4H), 2.13 (m, 4H). LCMS (method B): [MH]+=481.1, tR=1.66 min.

Workup

customSolvent was evaporated
customthe crude product was purified on HPLC (neutralized to free base)

Sources & evidence

ORD record: ord-cd1aed3809a644b99ecbe1ce56969bf1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497368B2

Reaction notes

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