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Piperidine → HCID 44541049, compound

HRID 1616022
Notes
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Reaction equation

HRID 1616022 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:20]=[C:19]([C:21]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:22]=3[CH:23]=[CH:24][NH:25]4)[CH:18]=[C:17]3[C:13]=2[CH:14]=[N:15][NH:16]3)=[O:10])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[Cl:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:20]=[C:19]([C:21]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:22]=3[CH:23]=[CH:24][NH:25]4)[CH:18]=[C:17]3[C:13]=2[CH:14]=[N:15][NH:16]3)=[O:10])=[N:4][C:5]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 44540871HCID 44540871, compound

Product 1

HCID 44541049HCID 44541049, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 22036561
Dimethyl sulfoxide methanol
Solvent

Conditions

Temperature
160 °C

Procedure

To a microwave vial was added 2 ml of a solution of 3,6-dichloro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (306 mg, 0.71 mmol) in DMSO (6 ml). Piperidine (0.024 ml, 0.25 mmol) and DIPEA (0.129 ml) were added and the mixture was heated at 160° C. for 2 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 further purified by Mass Directed Automated Preparative HPLC (Method E) and product-containing fractions were dried under a stream of nitrogen to afford the title compound (22 mg).

Workup

  1. customThe crude reaction mixture
  2. custompurified by Mass Directed Automated Preparative HPLC (Method E)
  3. customThe sample was further purified by Mass Directed Automated Preparative HPLC (Method E)
  4. additionproduct-containing fractions
  5. customwere dried under a stream of nitrogen

Sources & evidence

ORD record
ord-fb7d15f9d66844febba7d340c401a6ff
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765743B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes