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Dimethylamine → HCID 44541050, compound

HRID 1616023
Notes
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Reaction equation

HRID 1616023 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.[CH3:30][NH:31][CH3:32].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:31]([CH3:32])[CH3:30])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 44540871HCID 44540871, compound

Product 1

HCID 44541050HCID 44541050, compoundYield 13.9%

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). Dimethylamine (2M in THF, 0.123 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 (15 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-b5e72477826e4a7c93783ebaeda0b46d
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