1,1'-Carbonyldiimidazole → HCID 67523955, compound

HRID 659034Notes

Reaction equation

HRID 659034 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].NC1[CH:15]=[C:16]([CH:20]([CH3:23])[C:21]#[N:22])[CH:17]=[CH:18]C=1.NC1C=[CH:41][C:28]([O:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32]([NH:36][CH2:37][CH2:38][CH2:39][OH:40])[N:31]=2)=[CH:27][CH:26]=1>ClCCl>[C:21]([CH:20]([CH3:23])[C:16]1[CH:15]=[C:12]([NH:8][C:1]([NH:3][C:7]2[CH:6]=[CH:41][C:28]([O:29][C:30]3[CH:35]=[CH:34][N:33]=[C:32]([NH:36][CH2:37][CH2:38][CH2:39][OH:40])[N:31]=3)=[CH:27][CH:26]=2)=[O:2])[CH:11]=[CH:18][CH:17]=1)#[N:22]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 134713392-(3-Aminophenyl)propanenitrileHCID 67524085HCID 67524085, compound

Product 1

HCID 67523955HCID 67523955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

222 mg (1.37 mmol) 1,1′-Carbonyl-diimidazol (CDI) were given to a solution of 182 mg (1.24 mmol) 2-(3-amino-phenyl)-propionitrile in 4.0 ml dichloro-methane and stirred for 12 h. A solution of 324 mg (1.24 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 6 ml dichloromethane was added within 30 min. and the mixture stirred for 12 h at r.t. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel (dichloromethane/ethanol 96:4). The obtained material was leached with ether, filtered and dried. Yield 200 mg (37%) of the title compound.

Workup

  1. stirringthe mixture stirred for 12 h at r.t
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by chromatography on silica gel (dichloromethane/ethanol 96:4)
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-a5274111bdec4beb9421dc0a94f2ccec
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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