1,1'-Carbonyldiimidazole → HCID 15513093, compound

HRID 1635924Notes

Reaction equation

HRID 1635924 reaction equation
[CH3:1][C@H:2]([NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C:3]([OH:5])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:29][C:30]1[NH:34][N:33]=[C:32]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[C:31]=1[C:42]1[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=1>O1CCCC1>[C:7]([NH:6][C@H:2]([C:3]([NH:29][C:30]1[C:31]([C:42]2[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=2)=[C:32]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[NH:33][N:34]=1)=[O:5])[CH3:1])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 736104N-carbobenzyloxyalanineHCID 178509109HCID 178509109, compound

Product 1

HCID 15513093HCID 15513093, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a stream of argon gas, 421 mg of Z-L-alanine and 306 mg of carbonyldiinidazole (CDI) were dissolved in 10 ml of tetrahydrofuran, followed by stirring at room temperature for 10 minutes. Then, 150 mg of 5-amino-3-(4-fluorophenyl)-4-(4-pyridyl)pyrazole and 287 mg of 1,8-diazabicyclo[5.4.2]undec-7-ene (DBU) were added thereto, followed by stirring at room temperature for 4 hours. After the reaction mixture was concentrated under reduced pressure, the resulting residue was purified by column chromatography using 20 g of silica gel [with an elution solvent comprising chloroform-methanol (50:1)]. Thus, 88 mg (32% yield) of the title compound was obtained as a white powder.

Workup

  1. stirringby stirring at room temperature for 4 hours
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-1db4869bbb6341f4ab6d0220614f3373
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

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