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2-Methylbenzenesulfonic acid → 1,2,4-Triazolo[3,4-f][1,6]naphthyridine, 9-phenyl-8-[4-[[4-[5-(2-pyridinyl)-1H-1,2,4-triazol-3-yl]-1-piperidinyl]methyl]phenyl]-

HRID 1678760
Notes
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Reaction equation

HRID 1678760 reaction equation
[C:1]1([C:7]2[C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:31][CH2:30][CH:29]([C:32]5[NH:36][C:35]([C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=6)=[N:34][N:33]=5)[CH2:28][CH2:27]4)=[CH:21][CH:20]=3)=[N:9][C:10]3[C:15]([CH:16]=2)=[C:14]([NH:17][NH2:18])[N:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:43](OOC)(OOC)OOC.C1(C)C(S(O)(=O)=O)=CC=CC=1>CO.C1(C)C=CC=CC=1>[C:1]1([C:7]2[C:8]([C:19]3[CH:20]=[CH:21][C:22]([CH2:25][N:26]4[CH2:27][CH2:28][CH:29]([C:32]5[NH:36][C:35]([C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=6)=[N:34][N:33]=5)[CH2:30][CH2:31]4)=[CH:23][CH:24]=3)=[N:9][C:10]3[CH:11]=[CH:12][N:13]4[CH:43]=[N:18][N:17]=[C:14]4[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 21973508Trimethoxy orthoformateHCID 178514340HCID 178514340, compound

Product 1

HCID 1784200531,2,4-Triazolo[3,4-f][1,6]naphthyridine, 9-phenyl-8-[4-[[4-[5-(2-pyridinyl)-1H-1,2,4-triazol-3-yl]-1-piperidinyl]methyl]phenyl]-

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 1140TolueneSolvent

Procedure

To a solution of 8-9 (4.5 g, 8.1 mmol) in 20 mL methanol and 60 mL toluene was added trimethoxy orthoformate (3.5 g, 32.5 mmol) and toluenesulfonic acid (0.1 g, 0.8 mmol). The mixture was refluxed for 10 hrs. Upon removal of the solvent, the residue was purified by flash column chromatography (100% CHCl3 to 50% CHCl3 and 50% methanol) to afford the desired product 8-10.

Workup

  1. temperatureThe mixture was refluxed for 10 hrs
  2. customUpon removal of the solvent
  3. customthe residue was purified by flash column chromatography (100% CHCl3 to 50% CHCl3 and 50% methanol)

Sources & evidence

ORD record
ord-a308e9f9b8a64ca0b1874e50d2656307
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08008317B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes