1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69482645, compound

HRID 2364441Notes

Reaction equation

HRID 2364441 reaction equation
[CH2:1]([O:3][C:4](=[O:42])[CH2:5][C:6]([N:8]([CH2:28][CH2:29][N:30]([CH3:41])[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C:9]1[C:10]([C:23]([O:25]CC)=O)=[N:11][CH:12]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:14]=1)=[O:7])[CH3:2].C1CCN2C(=NCCC2)CC1.OS([O-])(=O)=O.[Na+]>CCO.O>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C:13]2[CH:14]=[C:9]3[C:10]([C:23]([OH:25])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:42])[C:6](=[O:7])[N:8]3[CH2:28][CH2:29][N:30]([CH3:41])[C:31]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:32])=[N:11][CH:12]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516919Sodium BisulfateHCID 69480274HCID 69480274, compound

Product 1

HCID 69482645HCID 69482645, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 3-{[3-(ethyloxy)-3-oxopropanoyl][2-(methyl {[(phenylmethyl)oxy]carbonyl}amino)ethyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (1.32 g, 2.3 mmol) in EtOH (25 mL) under nitrogen was treated with DBU (0.54 mL, 3.55 mmol). After stirring at ambient temperature for 5 min., the reaction mixture was treated with 1N NaHSO4 (3.6 mL). The resulting slurry was diluted with water, filtered, the filtered solid was washed with 1:1 water:EtOH, and Et2O and thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (q, J=6.96 Hz, 3 H), 2.84 (d, J=15.02 Hz, 3 H), 3.42-3.50 (m, 1 H), 3.54 (t, J=4.94 Hz, 1 H), 4.03 (s, 1 H), 4.14 (s, 1 H), 4.19-4.27 (m, 2 H), 4.32-4.38 (m, 2 H), 4.72 (s, 1 H), 4.93 (s, 1 H), 7.00 (d, J=4.21 Hz, 1 H), 7.10 (t, J=8.79 Hz, 2 H), 7.19-7.30 (m, 4 H), 7.30-7.39 (m, 2 H), 8.04 (s, 1 H), 8.41 (s, 1 H), 8.49 (s, 1 H); ES+ MS: 534 (M+H+).

Workup

  1. filtrationfiltered
  2. washthe filtered solid was washed with 1:1 water
  3. dry with materialEtOH, and Et2O and thoroughly dried under high vacuum

Sources & evidence

ORD record
ord-6fdd805ce2594b039e3386b312e9dbfe
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…