Toluene → N-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)-2,3-dihydro-1,4-benzodioxine-6-carboxamide

HRID 2035736Notes

Reaction equation

Br[C:2]1[C:7]2=[N:8][S:9](=[O:13])(=[O:12])[CH2:10][CH2:11][N:6]2[CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[O:21]1[CH2:26][CH2:25][O:24][C:23]2[CH:27]=[C:28]([C:31]([NH2:33])=[O:32])[CH:29]=[CH:30][C:22]1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:12]=[S:9]1(=[O:13])[CH2:10][CH2:11][N:6]2[CH:5]=[CH:4][CH:3]=[C:2]([NH:33][C:31]([C:28]3[CH:29]=[CH:30][C:22]4[O:21][CH2:26][CH2:25][O:24][C:23]=4[CH:27]=3)=[O:32])[C:7]2=[N:8]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 9-bromo-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (100 mg) in DMF (1 ml) were added toluene (2 mL), 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide (74.9 mg), cesium carbonate (248 mg), 9,9-dimethyl-4,5-(diphenylphosphino)xanthene (33.0 mg) and tris(dibenzylideneacetone)dipalladium(0) (34.8 mg) at room temperature. The reaction mixture was stirred under a nitrogen atmosphere at 100° C. for 5 hr, and purified by silica gel column chromatography (methanol/ethyl acetate) and recrystallized from (methanol/diisopropyl ether) to give the title compound (25.4 mg).

Workup

custompurified by silica gel column chromatography (methanol/ethyl acetate)
customrecrystallized from (methanol/diisopropyl ether)

Sources & evidence

ORD record: ord-abf0ef1c637846c993f79b81b711609c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575154B2

Reaction notes

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