2-Butene, 1-bromo-3-methyl- → HCID 10137603, compound

HRID 381895Notes

Reaction equation

HRID 381895 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([NH2:31])(=[O:30])=[O:29])=[C:24]([F:32])[CH:23]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6]C=CC=1.Br[CH2:34]C=C(C)C>>[CH3:6][C:7]([CH3:34])=[CH:2][CH2:1][N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([NH2:31])(=[O:29])=[O:30])=[C:24]([F:32])[CH:23]=2)[CH:10]=[N:9]1

Participants

3

Reactant 2

HCID 700922-Butene, 1-bromo-3-methyl-HCID 21934239HCID 21934239, compound

Product 1

HCID 10137603HCID 10137603, compoundYield 30%

Procedure

2-Benzyl-4-(4-fluorophenyl)-5-[3-fluoro-4-(aminosulfonyl)phenyl]-3(2H)-pyridazinone, prepared according to the method of Example 68, was N-debenzylated according to the method of Example 11. The intermediate was N-alkylated according to the method of Example 20, substituting 1-bromo-3-methyl-2-butene in place of 4-fluorobenzyl bromide, to provide the title compound (yield: 50 mg, 30%). mp 134-136° C. 1H NMR (300 MHz, CDCl3) δ 1.79 (s, 3H), 1.86 (s, 3H), 4.78 (s, 2H), 4.85 (d, J=7.5 Hz, 2H), 5.48 (t, J=6 Hz, 1H), 6.96 (t, J=9 Hz, 2H), 7.18 (dd, J=9 Hz, 6 Hz, 2H), 7.28 (d, J=9 Hz, 2H), 7.83 (s, 1H), 7.85 (d, J=9 Hz, 2H). MS (DCI/NH3) m/z 414 (M+H)+. Anal. calc. for C21H20FN3O3S: C, 61; H, 4.87; N, 10.16. Found: C, 60.98; H, 4.66; N, 9.95.

Sources & evidence

ORD record
ord-7c83c9f366974364a9b596704474c4e8
Source dataset
uspto-grants-2001_10
Patent number
US06307047B1

Reaction notes

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