Benzyl azide → HCID 86731672, compound

HRID 1504781Notes

Reaction equation

HRID 1504781 reaction equation
O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[C:14]([C:16]1[N:21]=[C:20]([NH2:22])[CH:19]=[CH:18][CH:17]=1)#[CH:15].[CH2:23]([N:30]=[N+:31]=[N-:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.C(O)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:23]([N:30]1[CH:15]=[C:14]([C:16]2[N:21]=[C:20]([NH2:22])[CH:19]=[CH:18][CH:17]=2)[N:32]=[N:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 450797916-Ethynylpyridin-2-amine

Product 1

HCID 86731672HCID 86731672, compound

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium ascorbate (34 mg, 0.17 mmol) and copper (II) sulfate pentahydrate (11 mg, 0.042 mmol) were added to a solution of 6-ethynylpyridine-2-amine (100 mg, 0.85 mmol) and benzyl azide (113 mg, 0.846 mmol) in water (5 mL) and ethanol (5 mL). The reaction mixture was stirred vigorously in the absence of light for 14 hours. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10-100% ethyl acetate/hexanes, linear gradient) to afford 6-(1-benzyl-1H-1,2,3-triazol-4-yl)pyridin-2-amine. MS ESI calc'd. for C14H14N5 [M+H]+ 252. found 252. 1H NMR (500 MHz, CD3OD) δ 8.21 (s, 1H), 7.49-7.44 (m, 1H), 7.37-7.26 (m, 5H), 7.22 (d, J=7.4 Hz, 1H), 6.49 (d, J=8.2 Hz, 1H), 5.58 (s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (10-100% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-9a56cf6f546140fcbf5adad514e4900e
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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