1,1'-Carbonyldiimidazole → HCID 24997650, compound

HRID 658999Notes

Reaction equation

HRID 658999 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:17]1[CH:18]=[C:19](C=C[CH:23]=1)N)([CH3:16])([CH3:15])[CH3:14].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:13]([C:17]1[CH:23]=[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:19][CH:18]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 793343-tert-ButylanilineHCID 67524085HCID 67524085, compound

Product 1

HCID 24997650HCID 24997650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

172 mg (1.06 mmol) 1,1′-Carbonyl-diimidazol (CDI) were given to a solution of 144 mg (0.964 mmol) 3-t-butylaniline in 4.0 ml dichloromethane and stirred for 12 h. A solution of 263 mg (0.964 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 6.0 ml dichloromethane was added within 30 min. and the mixture stirred for 12 h at r.t. The reaction mixture was filtered, the filtrate evaporated and the residue purified by chromatography on silica gel (dichloromethane/methanol 95:5). The obtained material was washed with ether and the precipitate was isolated by filtration and dried. Yield: 170 mg (41%) of the title compound.

Workup

  1. stirringthe mixture stirred for 12 h at r.t
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate evaporated
  4. customthe residue purified by chromatography on silica gel (dichloromethane/methanol 95:5)
  5. washThe obtained material was washed with ether
  6. customthe precipitate was isolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-b8b6ffc29f274029bcbfeaac998c81fe
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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