Dimethylformamide → HCID 66580567, compound

HRID 1521839Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[S:19](=[O:22])(=[O:21])[CH2:20][C:11]=3[C:10]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(CC(=O)C)(=O)C.C[N:45](C=O)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N:25]1([C:23]([C:10]2[C:11]3[CH2:20][S:19](=[O:22])(=[O:21])[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[C:12]=3[N:8]([C:4]3[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=3)[NH2:45])[N:9]=2)=[O:24])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 90 °C

Procedure

1-(3-Bromophenyl)-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (0.15 g, 0.308 mmol), copper acetate (6 mg, 0.03 mmol), cesium carbonate (200 mg, 0.616 mmol) and acetyl acetone (13 μL, 0.123 mmol) are taken DMF purged with NH3 gas. The reaction mixture is heated to 90° C. for 24 h. After this time, reaction mixture is concentrated under reduced pressure and purified by column chromatography (100% EtOAc) to afford the title compound as a pale brown solid. 1H NMR (400 MHz, DMSO-d6) δ=7.99-7.97 (m, 1H), 7.62-7.60 (m, 1H), 7.24-7.20 (t, J=7.84 Hz, 1H), 6.98-6.95 (m, 1H), 6.75-6.73 (d, J=9.32 Hz, 1H), 6.58-6.56 (m, 2H), 5.57 (s, 2H), 4.87 (s, 2H), 3.95 (m, 2H), 3.66 (m, 6H), MS (ESI+): 425.0. HPLC (max plot): 94.69%; Rt 2.65 min.

Workup

custompurged with NH3 gas
customAfter this time, reaction mixture
concentrationis concentrated under reduced pressure
custompurified by column chromatography (100% EtOAc)

Sources & evidence

ORD record: ord-59ffd7f8fd61401cb10823e15f960bef
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073940B2

Reaction notes

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