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Toluene → 8-[4-(1,3-Dioxolan-2-yl)phenyl]9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

HRID 1678739
Notes
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Reaction equation

HRID 1678739 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[NH:28][NH2:29])[N:13]=2)=[CH:8][CH:7]=1.O.[C:31]1(C)C(S(O)(=O)=O)=CC=CC=1.C1(C)C=CC=CC=1.C(OC)(OC)OC>CO>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18]4=[N:28][N:29]=[CH:31][N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 9005Trimethyl orthoformateHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 594729242-[4-(1,3-dioxolan-2-yl)phenyl]-5-hydrazinyl-3-phenyl-1,6-Naphthyridine

Product 1

HCID 594728818-[4-(1,3-Dioxolan-2-yl)phenyl]9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of [2-(4-[1,3]dioxolan-2-yl-phenyl)-3-phenyl-[1,6]naphthyridin-5-yl]-hydrazine (3-4, 1.6 g, 4.2 mmol) and toluenesulfonic acid monohydrate (79 mg, 0.4 mmol) in 3:1 toluene:MeOH (16 mL) was added trimethyl orthoformate (0.58 mL, 12.5 mmol). The mixture was heated to 100° C. in a microwave reactor for 1 hr. The reaction mixture was then concentrated in vacuo. The solid was collected and dried with toluene azeotropically to give the title compound which was used for next step without further purification. LRMS m/z (M+1) Calcd: 395.1. Found 395.2.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customThe solid was collected
  3. dry with materialdried with toluene azeotropically

Sources & evidence

ORD record
ord-d0519a28af8140cc8cda374f97c44c00
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08008317B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes