1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69482061, compound

HRID 2364220Notes

Reaction equation

HRID 2364220 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][N:15]([C:35](=[O:42])[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:16]1[C:17]([C:30](OCC)=[O:31])=[N:18][CH:19]=[C:20]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH:21]=1.C1CCN2C(=NCCC2)CC1.OS([O-])(=O)=O.[Na+]>CCO.O>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH2:13][CH2:14][N:15]1[C:16]2[C:17](=[N:18][CH:19]=[C:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH:21]=2)[C:30]([OH:31])=[C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:35]1=[O:42]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516919Sodium BisulfateHCID 69480438HCID 69480438, compound

Product 1

HCID 69482061HCID 69482061, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 3-{[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl][3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (1.17 g, 2.04 mmol) in EtOH (10 mL) under nitrogen was treated with DBU (0.45 mL, 3.05 mmol). After stirring at ambient temperature for 15 min., the reaction mixture was treated with 1N NaHSO4 (3.1 mL). The resulting slurry was diluted with water, filtered and dried under high vacuum to provide the title compound as a white solid: 1H NMR (CDCl3) δ 13.93 (1H, b), 8.51 (1H, s), 7.82-7.86 (2H, m), 7.71-7.75 (2H, m), 7.36 (1H, s), 7.12 (2H, m), 6.99 (2H, t, J=9 Hz), 4.49 (2H, q, J=7 Hz), 4.22 (2H, t, J=7 Hz), 4.08 (2H, s), 3.79 (2H, t, J=7 Hz), 1.96-2.07 (2H, m), 1.45 (3H, t, J=7 Hz); ES+ MS: 530 (M+H+).

Workup

  1. filtrationfiltered
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-c2a73cc287d04549933306834a0a9fb7
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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