Dimethylformamide → HCID 66580567, compound

HRID 1521870Notes

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>>[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]([NH2:45])[CH:7]=[CH:6][CH:5]=3)[N:9]=2)=[O:24])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 10796Cesium carbonate

HCID 31261Acetylacetone

HCID 66578659HCID 66578659, compound

Product 1

HCID 66580567HCID 66580567, compound

Conditions

Temperature: 90 °C

Procedure

1-(3-bromophenyl)-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (150 mg, 0.31 mmol), cupric acetate (6.1 mg, 0.031 mmol), cesium carbonate (200 mg, 0.616 mmol) and acetyl acetone (13 □L, 0.123 mmol) are taken in a sealed tube to which is added a solution of 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 silica gel column chromatography (100% EtOAc) to afford the title compound as a pale brown solid. 1H NMR (DMSO-d6, 400 MHz): δ 7.99-7.97 (m, 1H), 7.62-7.60 (m, 1H), 7.24-7.20 (t, J=7.8 Hz, 1H), 6.98-6.95 (m, 1H), 6.75-6.73 (d, J=9.3 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 silica gel column chromatography (100% EtOAc)

Sources & evidence

ORD record: ord-3bd3ef7c3d034224a3c048b7c3523c4d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073940B2

Reaction notes

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