1,1'-Carbonyldiimidazole → HCID 136621555, compound

HRID 705377Notes

Reaction equation

HRID 705377 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:10](/[C:11](=[N:13]/[OH:14])/[NH2:12])=[C:4]2[CH:3]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].N12CCCN=C1CCCCC2>O1CCOCC1.Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:10]([C:11]3[NH:12][C:23](=[O:24])[O:14][N:13]=3)=[C:4]2[CH:3]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 89954954HCID 89954954, compound

Product 1

HCID 136621555HCID 136621555, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 19G (0.74 g, 2.049 mmol), 1,1′-carbonyldiimidazole (0.365 g, 2.254 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.340 mL, 2.254 mmol) in dioxane (10 mL) was refluxed for 1 hour, cooled and diluted with 1 M aqueous HCl. The resulting solid was collected by filtration, washed with water and dried. The solid was triturated twice with 1% methanol in dichloromethane to give the title compound (0.62 g, 78%). MS (ESI+) m/z 387/389 (M+H)+.

Workup

  1. temperaturecooled
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe solid was triturated twice with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-5ec46ff1b4ce4a059ee795180c966957
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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