Cesium carbonate → HCID 89761826, compound

HRID 528635Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.F[C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([NH2:34])=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:30]4[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=4[C:32]([NH2:34])=[O:33])[CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of INTERMEDIate M (900 mg, 2.08 mmol) and 2-fluorobenzamide (293 mg, 2.08 mmol, Aldrich) in DMF (10 mL) was added cesium carbonate (1.01 g, 3.12 mmol). The reaction mixture was heated at 90° C. for 48 h. After completion, the reaction mixture was diluted with ethyl acetate (30 mL) and water (20 mL). The layers were separated and the organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain crude material which was purified by combi flash silica gel column chromatography (column size: 40 g, elution: 25% ethyl acetate in hexane) to provide 2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)benzamide (800 mg, 71.4%); LCMS (ESI) m/z; 537.12 (M+H).

Workup

customThe layers were separated
dry with materialthe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customto obtain crude material which
customwas purified by combi flash silica gel column chromatography (column size: 40 g, elution: 25% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-a71c7d98a3114659a55adfc0561538bc
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346798B2

Reaction notes

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