Sodium hydride → Methyl 4-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-ylsulfonyl)butanoate

HRID 927247Notes

Reaction equation

[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH: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][CH:23]=2)[NH:3]1.[H-].[Na+].Cl[S:33]([CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])(=[O:35])=[O:34]>O1CCCC1.CN(C)C=O.O>[C:26]([C:25]1[CH:24]=[CH:23][C:22]([CH:4]2[N:3]([S:33]([CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])(=[O:35])=[O:34])[C:2](=[O:1])[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=3)[C:6]3[CH2:18][CH2:19][C:20](=[O:21])[C:5]2=3)=[CH:29][CH:28]=1)#[N:27]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile (example 1, 70 mg, 0.18 mmol) in a mixture of tetrahydrofuran (1.5 mL) and N,N-dimethylformamide (150 μL) is treated with sodium hydride (60% in mineral oil, 28 mg, 0.7 mmol) and stirred at room temperature for 5 min Methyl 4-(chlorosulfonyl)butanoate (106 mg, 0.53 mmol) is added, and the mixture is stirred at 50° C. over night. The mixture is diluted with water and N,N-dimethylformamide and purified by reversed phase HPLC (Wate7rs SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 48 mg; ESI mass spectrum [M+H]+=562; Retention time HPLC: 0.95 min (Z018_S04).

Workup

additionis added
custompurified by reversed phase HPLC (Wate7rs SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
custom0.95 min (Z018_S04)

Sources & evidence

ORD record: ord-daa02ad438ea472298f334fbaae32482
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290459B1

Reaction notes

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