HCID 71727006, compound → HCID 86696719, compound

HRID 2365863Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]([N:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][N:28]=[C:27](S(C)(=O)=O)[N:26]=2)=[CH:21][C:20]1=[O:35])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[CH:37]12[CH2:44][CH:40]([CH:41]([NH2:43])[CH2:42]1)[CH2:39][O:38]2>C(O)(CC)C>[CH:37]12[CH2:44][CH:40]([CH:41]([NH:43][C:27]3[N:26]=[C:25]([C:22]4[CH:23]=[CH:24][N:19]([C@@H:10]([C:11]5[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=5)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:20](=[O:35])[CH:21]=4)[CH:30]=[CH:29][N:28]=3)[CH2:42]1)[CH2:39][O:38]2

Participants

Conditions

Temperature: 130 °C

Procedure

A microwave vial was charged with (S)-1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2(1H)-one (100 mg, 0.190 mmol), 2-oxa-bicyclo[2.2.1]heptan-5-amine hydrochloride (53 mg, 0.47 mmol), TEA (0.50 mmol, 50 mg) and s-butanol (3.0 mL). The mixture was stirred at 130° C. under microwave irradiation for 3 hours. After completion of the reaction, the mixture was concentrated to give 4-(2-(2-oxabicyclo[2.2.1]heptan-5-ylamino)pyrimidin-4-yl)-1-((S)-2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)pyridin-2(1H)-one as an oil, which was used in the next step without further purification. LCMS (ESI) m/z: 571.3 [M+H]+.

Workup

customAfter completion of the reaction
concentrationthe mixture was concentrated

Sources & evidence

ORD record: ord-7b15425e014541bdb4d6feeb481f20df
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697715B2

Reaction notes

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