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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
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HRID 1678739 반응식
[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
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6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887
Methanol
용매

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온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d0519a28af8140cc8cda374f97c44c00
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08008317B2

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