Water → HCID 90310891, compound

HRID 927251Notes

Reaction equation

[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6]2[CH2:18][CH2:19][C:20](=[O:21])[C:5]=2[CH:4]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=2[S:30]([CH3:33])(=[O:32])=[O:31])[NH:3]1.[H-].[Na+].[CH3:36][S:37](Cl)(=[O:39])=[O:38].O>O1CCCC1>[CH3:33][S:30]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:22]=1[CH:4]1[N:3]([S:37]([CH3:36])(=[O:39])=[O:38])[C:2](=[O:1])[N:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([F:15])([F:17])[F:16])[CH:9]=2)[C:6]2[CH2:18][CH2:19][C:20](=[O:21])[C:5]1=2)[C:26]#[N:27])(=[O:31])=[O:32]

Participants

Conditions

Temperature: 50 °C

Procedure

4-(2,5-dioxo-1-(2-(trifluoromethyl)pyridin-4-yl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)-3-(methylsulfonyl)benzonitrile (example 15.6, 150 mg, 0.32 mmol) is added to a suspension of sodium hydride (60% in mineral oil, 35 mg, 0.88 mmol) in tetrahydrofuran (8.0 mL). After 10 min methanesulfonyl chloride (49 μL, 0.63 mmol) is added and the mixture is heated at 50° C. for 1.5 h. The mixture is cooled at room temperature and treated with water (1 mL). The mixture is stirred at room temperature for 30 min and purified by reversed phase HPLC (first purification: Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA; second purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 20 mg; ESI mass spectrum [M+H]+=555; Retention time HPLC: 0.90 min (Z011_S03).

Workup

temperatureThe mixture is cooled at room temperature
custompurified by reversed phase HPLC (first purification: Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA; second purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
custom0.90 min (Z011_S03)

Sources & evidence

ORD record: ord-8b89615c9b39497585fc7d33fb06e326
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290459B1

Reaction notes

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