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Water → HCID 58081353, compound

HRID 928435
Notes
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Reaction equation

HRID 928435 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([CH3:15])[CH:9]=2)=[N+:2]=[N-:3].[CH3:16][C:17]1[C:22]([CH2:23][NH:24][C:25](=[O:28])[CH2:26][CH3:27])=[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]=[N:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[C:10]([CH3:15])[CH:9]=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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962Water2×HCID 23667548Sodium AscorbateHCID 58081364HCID 58081364, compoundHCID 86661852HCID 86661852, compound

Product 1

HCID 58081353HCID 58081353, compound

Reagents, catalysts & solvents 2

HCID 24463
Copper sulfate pentahydrate
Catalyst
HCID 6386tert-ButanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 3-(azidomethyl)-7-methylquinoline (46.0 mg, 0.232 mmol) and tert-butyl (4,6-dimethyl-5-(propionamidomethyl)pyridin-2-yl)carbamate (70 mg, 0.231 mmol) in t-BuOH (1.8 ml)/water (1.8 ml) were added copper(II) sulfate pentahydrate (11.52 mg, 0.046 mmol) and sodium ascorbate (45.7 mg, 0.231 mmol). Reaction mixture was stirred overnight 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 a crude product, which was purified by silica gel chromatography (cyclohexane/ethyl acetate from 100/0 to 0/100) to afford the title compound. HPLC (Method G) Rt=1.408 min, MS (Method V) [M+H]+=502.4.

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 a crude product, which
  8. customwas purified by silica gel chromatography (cyclohexane/ethyl acetate from 100/0 to 0/100)

Sources & evidence

ORD record
ord-67a5055a59fd427ea02ad2f0d07e16fd
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290485B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes