Sodium Hydroxide → HCID 178425691, compound

HRID 226923Notes

Reaction equation

HRID 226923 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:18][C:19]#[CH:20])[CH:8]=1)=[O:6].[N:25](COC(=O)NC(C)(C)C)=[N+:26]=[N-:27].[OH-].[Na+]>C(O)(C)(C)C.O.[Cu].O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:18][C:19]2[N:25]=[N:26][NH:27][CH:20]=2)[CH:8]=1)=[O:6]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 57754544HCID 57754544, compoundHCID 57754756Azidomethyl N-(1,1-dimethylethyl)carbamate

Product 1

HCID 178425691HCID 178425691, compoundYield 54.6%

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

29 mg (0.092 mmol) of 3-(3,4-dimethyl-benzoyl)-1-prop-2-ynyl-1H-quinolin-4-one 4c (prepared as described by Paine, J. B.; J. Het. Chem. 1987, 351), 19 mg (0.11 mmol) of tert-butyl-carbamic acid azidomethyl ester, 5.0 mg (0.078 mmol) of copper powder, and 2.0 mg (0.008 mmol) of copper(II) sulfate pentahydrate were combined in a mixture of 0.5 mL tert-butanol and 0.2 mL water and stirred at 80° C. for 4 h. Then 70 mg (1.75 mmol) of sodium hydroxide in 1 mL water was added to that mixture and the resultant mixture was stirred at 80° C. for another hour. The mixture was filtered and purified using reverse phase HPLC (mobile phase with a gradient 15-80% acetonitrile in 50 min). Lyophilization of the HPLC fractions containing purified 4d provided 18 mg of a pale yellow product as the trifluoroacetate salt: LC-MSD, m/z for C21H18N4O2, [M+H]+=359.5, HPLC retention time: 1.5 min; 1H NMR (400 MHz, CDCl3): δ 2.25 (s, 3H), 2.3 (s, 3H), 6.7 (s, 2H), 7.1-7.2 (m, 1H), 7.4-7.45 (m, 1H), 7.45-7.5 (m, 2H), 7.75-7.85 (m, 3H), 8.4-8.5 (m, 1H), 8.65 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. custompurified
  3. customin 50 min
  4. additionLyophilization of the HPLC fractions containing
  5. custompurified 4d

Sources & evidence

ORD record
ord-3ddd6766cee245278f0e601b2226573b
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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