1-Methylpiperazine → HCID 67314419, compound

HRID 1011364Notes

Reaction equation

HRID 1011364 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[N:16][C:17]([CH:21]=[CH2:22])=[CH:18][CH:19]=2)[CH2:14][O:13]1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[N:16][C:17]([CH2:21][CH2:22][N:27]3[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]3)=[CH:18][CH:19]=2)[CH2:14][O:13]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 67314553HCID 67314553, compound

Product 1

HCID 67314419HCID 67314419, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Conditions

Temperature
100 °C

Procedure

Following the method described in Example 19, 5-fluoro-3-(2-vinyl-7H-furo[3,4-b]pyridin-5-ylidene)-1,3-dihydro-indol-2-one (60 mg, 0.20 mmol) and N-methylpiperazine (300 mg, 3.00 mmol) are heated 100° C. for 2 h. The reaction mixture is cooled and treated with triethylamine (10 drops). The reaction mixture is loaded onto silica gel and purified by chromatography (silica gel, gradient elution, 2% MeOH/Chloroform to 20% MeOH/chloroform ) to provide the title compound (80 mg, 100%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture is cooled
  2. custompurified by chromatography (silica gel, gradient elution, 2% MeOH/Chloroform to 20% MeOH/chloroform )

Sources & evidence

ORD record
ord-f1d23aa9e11d492e8d9a63319d6bdd45
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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