Ethylamine → HCID 44541048, compound

HRID 1616014Notes

Reaction equation

HRID 1616014 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.[CH2:29]([NH2:31])[CH3:30].CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[CH2:29]([NH:31][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)[CH3:30]

Participants

6

Reactant 3

HCID 6341Ethylamine5×HCID 81531Diisopropylethylamine3×HCID 44540963HCID 44540963, compound

Product 1

HCID 44541048HCID 44541048, compoundYield 3.2%

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). Ethylamine (0.021 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Further ethylamine (0.021 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Again, ethylamine (0.021 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 1 h under microwave irradiation. After this time ethylamine (0.021 ml, 0.26 mmol) and DIPEA (0.113 ml) were both added to the mixture and it was heated at 160° C. for 2 h under microwave irradiation. Finally, additional ethylamine (0.021 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 170° C. for 1 h under microwave irradiation. The crude reaction mixture was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method E). The sample was re-purified by Mass Directed Automated Preparative HPLC (Method E, using Waters Atlantis column 100 mm×19 mm, 5 um). Product-containing fractions were dried under a stream of nitrogen to afford the title compound (3.3 mg).

Workup

  1. temperaturethe mixture was heated at 160° C. for 2 h under microwave irradiation
  2. temperaturethe mixture was heated at 160° C. for 1 h under microwave irradiation
  3. additionboth added to the mixture and it
  4. temperaturewas heated at 160° C. for 2 h under microwave irradiation
  5. temperaturethe mixture was heated at 170° C. for 1 h under microwave irradiation
  6. customThe crude reaction mixture
  7. custompurified by Mass Directed Automated Preparative HPLC (Method E)
  8. customThe sample was re-purified by Mass Directed Automated Preparative HPLC (Method E, using Waters Atlantis column 100 mm×19 mm, 5 um)
  9. customProduct-containing fractions were dried under a stream of nitrogen

Sources & evidence

ORD record
ord-7958c17424ac4c3aaf167016e588e3d7
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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