1,1'-Carbonyldiimidazole → HCID 25002092, compound

HRID 659032Notes

Reaction equation

HRID 659032 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:21]=[CH:20]C(N)=C[CH:17]=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:17]=[CH:11][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:20][CH:21]=1)#[N:14]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileHCID 67524085HCID 67524085, compound

Product 1

HCID 25002092HCID 25002092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

188 mg (1.16 mmol) 1,1′-Carbonyl-diimidazol (CDI) were given to a solution of 175 mg (1.09 mmol) 4-(cyano-dimethyl-methyl)-phenylamine (Hicks, T. A., J. Med. Chem. 22 (1979) 1460-1464) in 4.0 ml dichloro-methane and stirred for 12 h. A solution of 284 mg (1.09 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 (ethyl acetate). The obtained material was left overnight with dichloromethane, the precipitate filtered, washed with ether and dried. Yield: 180 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 (ethyl acetate)
  4. waitThe obtained material was left overnight with dichloromethane
  5. filtrationthe precipitate filtered
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-2171d2f4921b44cebfd982d7720fac9f
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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