Ammonia → HCID 21934015, compound

HRID 381916Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][CH3:17])=[C:12](Br)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:19][S:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.N>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][CH3:17])=[C:12]([C:24]3[CH:25]=[CH:26][C:21]([S:20][CH3:19])=[CH:22][CH:23]=3)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Reactant 3

HCID 222Ammonia

HCID 27339594-(Methylthio)phenylboronic acid

HCID 21933858HCID 21933858, compound

Product 1

HCID 21934015HCID 21934015, compound

Procedure

The title compound is prepared according to the method of Example 6 starting with 2-(3-chloro-4-fluorophenyl)-4-methoxy-5-bromo-3(2H)-pyridazinone in place of 2-benzyl-5-methoxy-4-bromo-3(2H)-pyridazinone and substituting 4-(methylthio)benzeneboronic acid in place of 4-fluorobenzeneboronic acid (yield: 3.2 g, 63%). 1H NMR (300 MHz, CDCl3) δ 2.53 (s, 3H), 4.13 (s, 3H), 7.25 (t J=9 Hz, 1H), 7.35 (d, J=9 Hz 2H), 7.52 (d, J=9 Hz, 2H), 7.55-7.64 (m, 1H), 7.78 (dd, J=9 Hz, 3 Hz, 1H), 7.93 (s, 2H). MS (DCI/NH3) m/z 377 (M+H)+, 394 (M+NH4)+.

Sources & evidence

ORD record: ord-6933487c4c444094ae8b317bc7c1eac5
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06307047B1

Reaction notes

Loading…