1,1'-Carbonyldiimidazole → HCID 25002093, compound

HRID 659033Notes

Reaction equation

HRID 659033 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].[C:13]([C:15]([CH3:24])([CH3:23])[C:16]1[CH:17]=[C:18](N)C=C[CH:21]=1)#[N:14].NC1C=[CH:42][C:29]([O:30][C:31]2[CH:36]=[CH:35][N:34]=[C:33]([NH:37][CH2:38][CH2:39][CH2:40][OH:41])[N:32]=2)=[CH:28][CH:27]=1>ClCCl>[C:13]([C:15]([CH3:23])([CH3:24])[C:16]1[CH:21]=[C:12]([NH:8][C:1]([NH:3][C:7]2[CH:6]=[CH:42][C:29]([O:30][C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH:37][CH2:38][CH2:39][CH2:40][OH:41])[N:32]=3)=[CH:28][CH:27]=2)=[O:2])[CH:11]=[CH:18][CH:17]=1)#[N:14]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 569657872-(3-Aminophenyl)-2-methylpropanenitrileHCID 67524085HCID 67524085, compound

Product 1

HCID 25002093HCID 25002093, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

196 mg (1.21 mmol) 1,1′-Carbonyl-diimidazol (CDI) were given to a solution of 176 mg (1.10 mmol) 3-(cyano-dimethyl-methyl)-phenylamine in 4.0 ml dichloro-methane and stirred for 12 h. A solution of 286 mg (1.10 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 74 mg (15%) 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-e92f36bb8f4846af8661efcaa349aa65
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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