Phenylacetic Acid → HCID 69375597, compound

HRID 1249777Notes

Reaction equation

HRID 1249777 reaction equation
[C:1]1([CH2:7][C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.[NH2:23][C:24]1[N:29]=[C:28]2[NH:30][CH:31]=[C:32]([CH:33]=[C:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:35]([NH2:37])=[O:36])[C:27]2=[CH:26][CH:25]=1>ClCCl>[C:1]1([CH2:7][C:8]([NH:23][C:24]2[N:29]=[C:28]3[NH:30][CH:31]=[C:32]([CH:33]=[C:34]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:35]([NH2:37])=[O:36])[C:27]3=[CH:26][CH:25]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69376670HCID 69376670, compound

Product 1

HCID 69375597HCID 69375597, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

500 mg (3.67 mmol) of phenylacetic acid were dissolved in 20 ml of dichloromethane and 705 mg (3.67 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride were added at 0° C. The mixture is maintained at the same temperature for 30 minutes and then a solution of 680 mg (2.44 mmol) of 3-(6-amino-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenyl-propenamide in 10 ml of dichloromethane was added dropwise. After 6 hours at room temperature the mixture was washed with aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate and evaporated. The residue was chromatographed on a silica gel column by using a mixture cyclohexane/ethylacetate 4/1 to give 626 mg (65% yield) of the title compound.

Workup

  1. temperatureThe mixture is maintained at the same temperature for 30 minutes
  2. washAfter 6 hours at room temperature the mixture was washed with aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-7954cbad4e5e4cc08e9b7954cb262f68
Source dataset
uspto-grants-2002_01
Patent number
US06335342B1

Reaction notes

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