Water → HCID 86731263, compound

HRID 2277203Notes

Reaction equation

Cl[C:2]1[C:7]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[C:14]([F:16])[C:13]([O:17][CH2:18][CH:19]3[CH2:21][CH2:20]3)=[C:12]([F:22])[CH:11]=2)=[CH:6][N:5]=[C:4]([O:24][CH2:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[Cu]I>[CH:19]1([CH2:18][O:17][C:13]2[C:14]([F:16])=[CH:15][C:10]([C:9]3[O:23][C:2]4[CH:3]=[C:4]([O:24][CH2:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27])[N:5]=[CH:6][C:7]=4[N:8]=3)=[CH:11][C:12]=2[F:22])[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 160 °C

Procedure

A suspension of tert-butyl ((2S)-1-((4-chloro-5-((4-(cyclopropylmethoxy)-3,5-difluorobenzoyl)amino)pyridin-2-yl)oxy)propan-2-yl)carbamate (4.40 g), potassium carbonate (2.38 g) and copper(I) iodide (164 mg) in DMF (20 mL) was stirred at 160° C. for 4 hr under microwave irradiation. To the reaction mixture was added water, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and subjected to silica gel column chromatography (NH, ethyl acetate). The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.42 g).

Workup

extractionthe obtained mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
customThe solvent was evaporated
customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-af4d81b65c834148b30cb273faeba411
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133129B2

Reaction notes

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