Cesium carbonate → HCID 86686763, compound

HRID 1403133Notes

Reaction equation

[CH3:1][S:2][C:3]1[N:8]=[C:7](N2C3C=CC=CC=3N=C2C(F)F)[CH:6]=[C:5]([N:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[N:23]=[C:22]2[CH:30]([F:32])[F:31])[N:4]=1.[OH:33][CH2:34][C@H:35]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[F:31][CH:30]([F:32])[C:22]1[N:21]([C:5]2[N:4]=[C:3]([S:2][CH3:1])[N:8]=[C:7]([O:33][CH2:34][C@H:35]3[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36]3)[CH:6]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1,1′-[2-(methylsulfanyl)pyrimidine-4,6-diyl]bis[2-(difluoromethyl)-1H-benzimidazole] (2 g) in N,N-dimethylacetamide (10 mL) were added tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate (965 mg) and cesium carbonate (2.1 g), followed by stirring at 60° C. for 5 hours. After the completion of the reaction, to the reaction solution was added ice water and the precipitated solid was collected by filtration. After drying, the resultant was dissolved in dichloromethane and purified by silica gel column chromatography (hexane:ethyl acetate=90:10-65:35) to obtain tert-butyl (3S)-3-[({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(methylsulfanyl)pyrimidin-4-yl}oxy)methyl]pyrrolidine-1-carboxylate (2.01 g).

Workup

customAfter the completion of the reaction
filtrationthe precipitated solid was collected by filtration
customAfter drying
dissolutionthe resultant was dissolved in dichloromethane
custompurified by silica gel column chromatography (hexane:ethyl acetate=90:10-65:35)

Sources & evidence

ORD record: ord-c7cf64251b204048bbfc4128c439ce19
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912180B2

Reaction notes

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