Water → HCID 86680893, compound

HRID 2042949Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH:11]=[N:10][CH:9]=[N:8]1.CC1C=CC(S(O[CH2:23][C@@H:24]2[C@@H:29]([OH:30])[C@H:28]([OH:31])[C@@H:27]([OH:32])[C@H:26]([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[S:42][C:43]([C:46]5[O:47][CH:48]=[CH:49][CH:50]=5)=[CH:44][N:45]=4)[CH:34]=3)[O:25]2)(=O)=O)=CC=1.O>CN(C=O)C>[N:7]1([CH2:23][C@@H:24]2[C@@H:29]([OH:30])[C@H:28]([OH:31])[C@H:27]([OH:32])[C@H:26]([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[S:42][C:43]([C:46]5[O:47][CH:48]=[CH:49][CH:50]=5)=[CH:44][N:45]=4)[CH:34]=3)[O:25]2)[CH:11]=[N:10][CH:9]=[N:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

Cesium carbonate (660 mg, 2.02 mmol) was added to the solution of 1,2,4-triazole (140 mg, 2.02 mmol) in DMF (2.0 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h. The solution of toluenesulfonate 90 (240 mg, 0.41 mmol) in DMF (1.0 mL) was added to the reaction mixture. The reaction mixture was warmed up to room temperature, stirred at room temperature for 3 d. H2O was added to the reaction mixture and then extracted with EtOAc. The organic extract was dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by prep HPLC (C18) provided desired triazole 97 (28 mg, 14%) as a solid.

Workup

temperatureThe reaction mixture was warmed up to room temperature
stirringstirred at room temperature for 3 d
extractionextracted with EtOAc
extractionThe organic extract
dry with materialwas dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by prep HPLC (C18)

Sources & evidence

ORD record: ord-b78692ddea5641b9b1f605a0bf2f4673
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586550B2

Reaction notes

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