1-Methylpiperazine → HCID 44540961, compound

HRID 1616017Notes

Reaction equation

HRID 1616017 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[NH:24]1[C:25]2[C:21](=[C:20]([C:18]3[CH:17]=[C:16]4[C:12]([CH:13]=[N:14][NH:15]4)=[C:11]([NH:10][C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([N:33]5[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]5)[N:7]=4)=[O:9])[CH:19]=3)[CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23]1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 44540963HCID 44540963, compound

Product 1

HCID 44540961HCID 44540961, compoundYield 10.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Conditions

Temperature
160 °C

Procedure

To a microwave vial was added 2 ml of a solution of 6-chloro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (350 mg, 0.90 mmol, prepared as described in Example 18) in DMSO (14 ml). 1-methylpiperazine (0.029 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 160° C. for 4 h under microwave irradiation. The crude reaction mixture was dissolved in DMSO/MeOH (1:1) and purified by using Mass Directed Automated Preparative HPLC (Method E). Product-containing fractions were dried under a stream of nitrogen to afford the title compound (12.8 mg).

Workup

  1. customThe crude reaction mixture
  2. custompurified
  3. customProduct-containing fractions were dried under a stream of nitrogen

Sources & evidence

ORD record
ord-68de07e260b44871b72dace56b19e74c
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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