1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(4-methanesulfonyl-piperidin-1-yl)-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole

HRID 41969Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:12][CH2:11]2)[C:3]=1[CH:4]=O.[CH3:20][S:21][C:22]1[N:27]=[C:26]([NH:28][NH2:29])[CH:25]=[CH:24][N:23]=1.C1CCN2C(=NCCC2)CC1>CS(C)=O>[CH3:19][S:16]([CH:13]1[CH2:14][CH2:15][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:2]3[C:3]=2[CH:4]=[N:29][N:28]3[C:26]2[CH:25]=[CH:24][N:23]=[C:22]([S:21][CH3:20])[N:27]=2)[CH2:11][CH2:12]1)(=[O:18])=[O:17]

Participants

Conditions

Temperature: 180 °C

Procedure

In a 50 ml, round bottom flask, 2-fluoro-6-(4-methanesulfonylpiperidine-1-yl)benzaldehyde (1.37 g, 4.8 mmol), N-(2-methylsulfanyl-pyrimidin-4-yl)-hydrazine (0.75 g, 4.8 mmol) and DBU (2.19 g, 14.4 mmol) were combined with DMSO (17 mL). The mixture was stirred at 180° C. for 1.5 hr in a microwave. The brown solution was blown to dryness and the residue was purified through ISCO flash column chromatography (30% to 100% ethyl acetate in hexanes) to provide 4-(4-methanesulfonyl-piperidin-1-yl)-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole as a pale orange solid (750 mg, 38.7% yield). LC-MS calcd for C18H21N5O2S2 (m/e) 403.11, obsd 404.0 (M+H).

Workup

customthe residue was purified through ISCO flash column chromatography (30% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-1bd90c8f362441568fe29296fa63e2fa
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536172B2

Reaction notes

Loading…