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

HRID 1678742Notes

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=C[CH:36]=1.C1(C)C=CC=CC=1.C(OC)(OC)(OC)C>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]=[C:31]([CH3:36])[N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1

Participants

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, 0.35 g, 0.91 mmol) and toluenesulfonic acid monohydrate (17 mg, 0.09 mmol) in 3:1 toluene:MeOH (4 mL) was added trimethyl orthoacetate (0.157 mL, 1.23 mmol). The mixture was heated to 100° C. in a microwave reactor for 75 min. 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: 409.2. Found 409.2.

Workup

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

Sources & evidence

ORD record: ord-2002d4ccd8a34f0f8ddcb794fe18c7d3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008317B2

Reaction notes

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