2,4-Dimethoxybenzylamine → N-(2,4-dimethoxybenzyl)-6-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)pyridazin-3-amine

HRID 2274842Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][C:18]([F:22])=[CH:19][CH:20]=4)[N:15]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:25])=[O:24])[CH:14]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:32][O:33][C:34]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:35]=1[CH2:36][NH2:37]>CN1C(=O)CCC1.CCOC(C)=O>[CH3:32][O:33][C:34]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:35]=1[CH2:36][NH:37][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][C:18]([F:22])=[CH:19][CH:20]=4)[N:15]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:25])=[O:24])[CH:14]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 3-(1-(6-chloropyridazin-3-yl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole (Intermediate 44; 136 mg; 0.30 mmol) and 2,4-dimethoxybenzylamine (100 mg; 0.60 mmol) in NMP (2 mL) was stirred at 200° C. for 2 hours under a microwave reactor. The reaction mixture was diluted with EtOAc (30 mL), washed water (10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered, concentrated, and purified by a silica gel column chromatography (petroleum ether/EtOAc=4/1 to 2/1) to afford 120 mg (68%) of the title compound as a white solid.

Workup

washwashed water (10 mL), brine (10 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by a silica gel column chromatography (petroleum ether/EtOAc=4/1 to 2/1)

Sources & evidence

ORD record: ord-0b4d3f355b584a5e8a222450ddb7c936
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126984B2

Reaction notes

Loading…