1,1'-Carbonyldiimidazole → HCID 67363416, compound

HRID 1916604Notes

Reaction equation

HRID 1916604 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[Br:13][C:14]1[CH:15]=[C:16]([NH2:28])[C:17]([NH:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:18][CH:19]=1>C1COCC1.C([O-])(O)=O.[Na+]>[Br:13][C:14]1[CH:19]=[CH:18][C:17]2[N:20]([CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[C:6](=[O:7])[NH:28][C:16]=2[CH:15]=1

Participants

5

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 62642302HCID 62642302, compound

Product 1

HCID 67363416HCID 67363416, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
40 °C

Procedure

600 mg (3.70 mmol) CDI are added to a solution of 853 mg (3.00 mmol) 4-bromo-N1-(2-pyrrolidin-1-yl-ethyl)-benzene-1,2-diamine in 20 mL THF at RT. The reaction solution is heated to 40° C. and stirred for 30 min at this temperature. A further 600 mg (3.70 mmol) CDI are added and the reaction is stirred for a further 30 min at 40° C. The solution is diluted with semisaturated NaHCO3 solution and the aqueous phase is extracted twice with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The residue is triturated with acetonitrile, the precipitate is filtered and dried in the air.

Workup

  1. stirringthe reaction is stirred for a further 30 min at 40° C
  2. extractionthe aqueous phase is extracted twice with EtOAc
  3. dry with materialThe organic phase is dried over MgSO4
  4. customThe residue is triturated with acetonitrile
  5. filtrationthe precipitate is filtered
  6. customdried in the air

Sources & evidence

ORD record
ord-a6bded1a82db4e118a7ae57fd4721c87
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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