Ammonia → HCID 21933935, compound

HRID 381981Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:25])[NH:11][N:12]=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH:5]=[CH:6][C:7]=1F.[F:26][C:27]1[CH:28]=[C:29](Br)[CH:30]=[CH:31][C:32]=1[F:33].N>>[F:26][C:27]1[CH:28]=[C:29]([N:11]2[C:10](=[O:25])[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[C:14]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=3)[CH:13]=[N:12]2)[CH:30]=[CH:31][C:32]=1[F:33]

Participants

Reactant 3

HCID 222Ammonia

HCID 676754-Bromo-1,2-difluorobenzene

HCID 15431537HCID 15431537, compound

Product 1

HCID 21933935HCID 21933935, compound

Procedure

The title compound was prepared as described in Example 62, starting with 4-(3,4-difluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone in place of 4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone and substituting 3,4-difluorobromobenzene in place of 1-bromo-4-fluorobenzene (yield: 185 mg, 46.5%). mp 182-185° C. 1H NMR (300 MHz, DMSO-d6) δ 3.23 (s, 3H), 6.98 (d, J=9 Hz, 1H), 7.18 (m, 2H), 7.32 (m, 1H), 7.52 (d, J=9 Hz, 2 H), 7.6 (m, 2H), 7.85 (m, 1H), 7.9 (d, J=9 Hz, 2H), 8.3 (s, 1H). MS (DCI/NH3) m/z 457 (M+H)+, 474 (M+NH4)+.

Sources & evidence

ORD record: ord-085d61e57cf0434b898ce70ed81dc903
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06307047B1

Reaction notes

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