O-(2-(Vinyloxy)ethyl)hydroxylamine → 4-(2-fluoro-4-(methylthio)phenylamino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxamide

HRID 15968

Reaction equation

HRID 15968 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[C:12]([C:20]([O:22]CC)=O)=[N:13][N:14]([CH3:19])[C:15](=[O:18])[C:16]=1[CH3:17].C([O:27][CH2:28][CH2:29][O:30][NH2:31])=C>>[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[C:12]([C:20]([NH:31][O:30][CH2:29][CH2:28][OH:27])=[O:22])=[N:13][N:14]([CH3:19])[C:15](=[O:18])[C:16]=1[CH3:17]

Participants

3

Reactant 2

HCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 66674013Ethyl 4-(2-fluoro-4-(methylthio)phenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylate

Product 1

HCID 166671584-(2-fluoro-4-(methylthio)phenylamino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxamideYield 78%

Procedure

The title compound was prepared in 78% yield (2 steps) by the procedures described in Example 166 (steps I and J) using ethyl 4-(2-fluoro-4-(methylthio)phenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylate (50 mg, 0.14 mmol) and O-(2-vinyloxy-ethyl)-hydroxylamine (44 mg, 0.43 mmol). MS APCI (−) m/z 381 (M−1) detected; 1H NMR (400 MHz, CD3OD) δ 7.10 (dd, 1H), 7.03 (dd, 1H), 6.87 (t, 1H), 3.99 (t, 2H), 3.79 (s, 3H), 3.74 (t, 2H), 2.47 (s, 3H), 1.74 (s, 3H).

Sources & evidence

ORD record
ord-0f76ebd3e9df454f9d069e65320cce68
Source dataset
uspto-grants-2010_06
Patent number
US07732616B2

Linked notes

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