O-(cyclopropylmethyl)hydroxylamine → 5-bromo-4-(4-bromo-2-fluorophenylamino)-N-(cyclopropylmethoxy)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide

HRID 2068905Notes

Reaction equation

HRID 2068905 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[N:5]=[C:4]([C:10]([O:12]C)=O)[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[F:22].[CH:23]1([CH2:26][O:27][NH2:28])[CH2:25][CH2:24]1>>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[N:5]=[C:4]([C:10]([NH:28][O:27][CH2:26][CH:23]2[CH2:25][CH2:24]2)=[O:12])[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[F:22]

Participants

3

Reactant 2

HCID 11182605O-(cyclopropylmethyl)hydroxylamineHCID 66674136Methyl 5-bromo-4-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate

Product 1

HCID 166672505-bromo-4-(4-bromo-2-fluorophenylamino)-N-(cyclopropylmethoxy)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamideYield 40%

Procedure

The title compound was prepared in 40% yield by the procedure described in Example 1 (step 1) using methyl 5-bromo-4-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate (31 mg, 0.071 mmol) and O-cyclopropylmethyl-hydroxylamine (20 mg, 0.23 mmol). MS APCI (−) m/z 487, 489, 491 (M−1, Br pattern) detected; 1H NMR (400 MHz, CD3OD) δ 7.38 (dd, 1H), 7.31 (dd, 1H), 7.05 (t, 1H), 3.82 (s, 3H), 3.65 (d, 2H), 1.13 (m, 1H), 0.58 (q, 2H), 0.31 (q, 2H).

Sources & evidence

ORD record
ord-b70ac45ed65944e280662e54007650fe
Source dataset
uspto-grants-2012_10
Patent number
US08299076B2

Reaction notes

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