Ethyl Acetate → ethyl 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoate

HRID 20561Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([O:24][C@@H:25]([CH3:28])[CH2:26][OH:27])[CH:23]=1)[C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12].[CH2:29]([O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][C:36](F)=[CH:35][CH:34]=1)[CH3:30].C(OCC)(=O)C>CC(N(C)C)=O>[OH:27][CH2:26][C@H:25]([CH3:28])[O:24][C:22]1[CH:23]=[C:8]([CH:9]=[C:10]([C:11]([NH:13][C:14]2[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=2)=[O:12])[CH:21]=1)[O:7][C:36]1[CH:37]=[CH:38][C:33]([C:32]([O:31][CH2:29][CH3:30])=[O:40])=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 130 °C

Procedure

Caesium carbonate (8.45 g, 26 mmol) was added to a mixture of 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide (4 g, 13 mmol) and ethyl-4-fluorobenzoate (2.33 g, 13 mmol) in dimethylacetamide (70 mL) and the stirred mixture heated at 130° C. for 72 hours. The mixture was allowed to reach RT and ethyl acetate (100 mL) added. The mixture was washed with water (5×40 mL), brine (40 mL), dried (MgSO4), filtered, and reduced in vacuo. The residue was chromatographed on silica, eluting with a gradient of 50% ethyl acetate in isohexane, to give the desired compound (0.18 g)

Workup

customto reach RT
washThe mixture was washed with water (5×40 mL), brine (40 mL)
dry with materialdried (MgSO4)
filtrationfiltered
customThe residue was chromatographed on silica
washeluting with a gradient of 50% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-c641fca714d7436f9429b7f80fe78e04
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745475B2

Reaction notes

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