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Triethylamine → HCID 178434267, compound

HRID 490100
Notes
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Reaction equation

HRID 490100 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[C:16](Cl)[N:17]=[N:18][CH:19]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([Sn](C)(C)C)[CH:29]=2)[NH:24][N:23]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[CH3:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:16]3[N:17]=[N:18][CH:19]=[C:14]([N:11]4[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]4)[N:15]=3)[CH:29]=2)[NH:24][N:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 576741865-(4-Boc-piperazin-1-yl)-3-chloro[1,2,4]triazineHCID 178434313HCID 178434313, compound

Product 1

HCID 178434267HCID 178434267, compoundYield 7.8%

Reagents, catalysts & solvents 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 5-(4-Boc-piperazin-1-yl)-3-chloro[1,2,4]triazine 151 (50 mg, 0.167 mmol.) in anhydrous DMF (3 mL) was added 3-methyl-5-trimethylstannanylindazole 152 (49 mg, 0.166 mmol.), tris(dibenzylideneacetone)dipalladium (15 mg, 0.016 mmol.), tri-o-tolylphosphine (10 mg, 0.033 mmol.) and triethylamine (17 mg, 0.168 mmol.). The reaction mixture was heated in a microwave reactor at 180° C. for 20 minutes. Ethyl acetate (50 mL) was added. The organic layer was washed with water and brine. The organic layer was filtered through Celite and dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 3-(3-methylindazol-5-yl)-5-(4-Boc-piperazin-1-yl)-[1,2,4]triazine 153 (5.1 mg, 0.013 mmol.).

Workup

  1. washThe organic layer was washed with water and brine
  2. filtrationThe organic layer was filtered through Celite
  3. dry with materialdried over sodium sulfate
  4. customThe organic solvent was evaporated under reduced pressure
  5. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-ec2fe657d51a4462b46fa39df0e076ec
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528132B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes