Dimethylamine → HCID 52950867, compound

HRID 1521867Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:13]=[C:14]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])[C:10]=3[CH2:9][S:8](=[O:30])(=[O:29])[C:6]=2[CH:7]=1.CC([O-])(C)C.[Na+].[CH3:37][NH:38][CH3:39]>C1(C)C=CC=CC=1.C1COCC1>[CH3:37][N:38]([CH3:39])[C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:13]=[C:14]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])[C:10]=3[CH2:9][S:8](=[O:30])(=[O:29])[C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

7-bromo-3-(morpholin-4-ylcarbonyl)-1-phenyl-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (100 mg, 0.20 mmol, 1 eq.), NaOtBu (280 mg, 0.29 mmol, 1.4 eq.) are taken in degassed toluene in a sealed tube. Tris(dibenylidene acetone)dipalladium(0) (5 mg, 0.005 mmol, 0.025 eq.), 2-ditertiary butyl phosphino-2′,4′,6′-triisopropyl biphenyl (3.5 mg, 0.008 mmol, 0.04 eq.) are then added followed by dimethylamine in THF (3 mL, 2 M) and the reaction mixture is heated at 90° C. for 16 h. After this time, reaction mixture is filtered through a celite pad, evaporated and purified by silica gel flash chromatography to afford the title compound as a pale brown solid. 1H NMR (DMSO-d6, 400 MHz): δ 7.61-7.59 (m, 3H), 7.51-7.49 (m, 2H), 7.10 (s, 1H), 6.81-6.79 (dd, J=2.6, 9.0 Hz, 1H), 6.61-6.59 (d, J=9.0 Hz, 1H), 4.76 (s, 2H), 3.96 (m, 2H), 3.65 (m, 4H), 3.59 (m, 2H), 2.97 (s, 6H). MS (ESI+): 453.0. HPLC (max plot) 91.39%; Rt 4.20 min.

Workup

customAfter this time, reaction mixture
filtrationis filtered through a celite pad
customevaporated
custompurified by silica gel flash chromatography

Sources & evidence

ORD record: ord-99bef32e76054f0b9fd881d41d423179
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073940B2

Reaction notes

Loading…