Water → HCID 58081212, compound

HRID 928431Notes

Reaction equation

HRID 928431 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH3:15])[CH:9]=[CH:8]2)=[N+:2]=[N-:3].[CH3:16][C:17]1[C:22]([CH2:23][NH:24][C:25](=[O:28])[C:26]#[CH:27])=[C:21]([CH3:29])[N:20]=[C:19]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:18]=1.O.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:16][C:17]1[C:22]([CH2:23][NH:24][C:25]([C:26]2[N:3]=[N:2][N:1]([CH2:4][C:5]3[CH:6]=[C:7]4[C:12](=[CH:13][CH:14]=3)[N:11]=[C:10]([CH3:15])[CH:9]=[CH:8]4)[CH:27]=2)=[O:28])=[C:21]([CH3:29])[N:20]=[C:19]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH:18]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 23667548Sodium AscorbateHCID 58081201HCID 58081201, compoundHCID 58081368HCID 58081368, compound

Product 1

HCID 58081212HCID 58081212, compound

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 6-(azidomethyl)-2-methylquinoline (58.9 mg, 0.297 mmol) and tert-butyl (4,6-dimethyl-5-(propiolamidomethyl)pyridin-2-yl)carbamate (90 mg, 0.297 mmol) in t-BuOH (2 ml)/water (2 ml) were added copper(II) sulfate pentahydrate (14.84 mg, 0.059 mmol) and sodium ascorbate (58.9 mg, 0.297 mmol). Reaction mixture was stirred for 1.5 h at 23° C. Reaction mixture was poured into water and extracted twice with ethyl acetate. Combined organic layers were washed with brine, dried over sodium sulfate and evaporated to afford the crude material, which was purified by silicagel chromatography (DCM/methanol from 10/0 to 9/1) to afford the title compound. HPLC (Method G) Rt=1.308 min; MS (Method F) [M+H]+=502.5

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. extractionextracted twice with ethyl acetate
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto afford the crude material, which
  8. customwas purified by silicagel chromatography (DCM/methanol from 10/0 to 9/1)

Sources & evidence

ORD record
ord-ae761b253628401c8d6de1b668b9d132
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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