Water → HCID 178458781, compound

HRID 1506177Notes

Reaction equation

[N:1]([CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:12]=[N:13][N:14]3[C:19]=2[C:18]2[CH:20]=[CH:21][NH:22][C:17]=2[N:16]=[CH:15]3)[CH2:7][CH2:6]1)=[N+:2]=[N-:3].[CH3:23][C:24]([OH:28])([C:26]#[CH:27])[CH3:25].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].O>ClCCl.S([O-])([O-])(=O)=O.[Cu+2]>[C:11]1([C@H:8]2[CH2:9][CH2:10][C@H:5]([CH2:4][N:1]3[CH:27]=[C:26]([C:24]([OH:28])([CH3:25])[CH3:23])[N:3]=[N:2]3)[CH2:6][CH2:7]2)[N:12]=[N:13][N:14]2[C:19]=1[C:18]1[CH:20]=[CH:21][NH:22][C:17]=1[N:16]=[CH:15]2

Participants

Conditions

Temperature: 80 °C

Procedure

1-[trans-4-(Azidomethyl)cyclohexyl]-7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidine (30.0 mg, 0.101 mmol) and 2-methyl-3-butyn-2-ol (12.0 μL, 0.122 mmol) in dichloromethane (3 mL) were mixed with copper(II) sulfate (24.0 mg, 0.152 mmol) and sodium ascorbate (60.0 mg, 0.304 mmol) and then stirred at 80° C. for 2 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→0/1-ethyl acetate/methanol=20/1 (v/v)) to give the title compound as a colorless solid (13.2 mg, yield 34%).

Workup

extractionthe reaction mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→0/1-ethyl acetate/methanol=20/1 (v/v))

Sources & evidence

ORD record: ord-f92711c7c0fb48a99c378f58702f95d9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216999B2

Reaction notes

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