1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68162215, compound

HRID 2366885Notes

Reaction equation

C1CCN2C(=NCCC2)CC1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[CH:21][N:22]([CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]=2)=[CH:15][CH:14]=1.[C:33]([NH:38][C:39](=[O:44])[O:40][CH:41]([CH3:43])[CH3:42])(=[O:37])/[CH:34]=[CH:35]/[CH3:36]>C(#N)C>[CH3:36][CH:35]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[CH:21][N:22]([CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]=2)=[CH:15][CH:14]=1)[CH2:34][C:33]([NH:38][C:39]([O:40][CH:41]([CH3:42])[CH3:43])=[O:44])=[O:37]

Participants

Conditions

Temperature: 50 °C

Procedure

DBU (954 mg, 944 μl, 6.26 mmol) was added to a stirred solution of 1,1-dimethylethyl 3-[4-(4-aminophenyl)-1H-imidazol-1-yl]propanoate (for a preparation see Intermediate 96) (1.8 g, 6.26 mmol) and 1-methylethyl (2E)-2-butenoylcarbamate (for a preparation see Intermediate 49) (1.34 g, 7.83 mmol) in acetonitrile (25 mL). The reaction mixture was stirred at 50° C. for 48 h then was cooled to room temperature and most of the solvent was removed in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 5% MeOH in AcOEt) gave 1,1-dimethylethyl 3-[4-(4-{[1-methyl-3-({[(1-methylethyl)oxy]carbonyl}amino)-3-oxopropyl]amino}phenyl)-1H-imidazol-1-yl]propanoate (1.53 g, 3.34 mmol, 53%) as an orange oil.

Workup

temperaturethen was cooled to room temperature and most of the solvent
customwas removed in vacuo
customPurification of the residue by flash chromatography on silica gel (gradient: 0 to 5% MeOH in AcOEt)

Sources & evidence

ORD record: ord-7e08ee3f62144466a416069a135a135b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697725B2

Reaction notes

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