Dimethyl Sulfoxide → HCID 59327063, compound

HRID 410324Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)=[CH:6][N:5]=[CH:4][N:3]=1.CS(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[C:40]([C:42]1[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=1)=[O:41]>O>[NH:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[C:40]([C:42]1[CH:47]=[CH:46][C:45]([O:48][C:2]2[C:7]([C:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=3)=[CH:6][N:5]=[CH:4][N:3]=2)=[CH:44][CH:43]=1)=[O:41]

Participants

Conditions

Temperature: 100 °C

Procedure

To a vial was added tert-butyl 4-(4-chloropyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (320 mg, 1.082 mmol), DMSO (5.4 mL), cesium carbonate (370 mg, 1.136 mmol), and (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (258 mg, 1.082 mmol) before sealing and heating to 100° C. for 45 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate before drying over magnesium sulfate, filtering, and concentrating under reduced pressure. The crude material was taken after purifying by column chromatography (10% methanol/dichloromethane), affording tert-butyl 4-(4-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate. MS (ESI, pos. ion) m/z: 498.3 (M+1).

Workup

extractionextracted with ethyl acetate
dry with materialbefore drying over magnesium sulfate
filtrationfiltering
concentrationconcentrating under reduced pressure
customafter purifying by column chromatography (10% methanol/dichloromethane)

Sources & evidence

ORD record: ord-7174c7e5472244a18400049f5da05bbd
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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