3-Pyridinemethanol → 4-(3-Bromo-4-fluorophenyl)-3-{4-[(pyridin-3-ylmethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one trifluoroacetate

HRID 82732

반응식

HRID 82732 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[C:16]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[N:17][O:18][N:19]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH2:27]([OH:34])[C:28]1[CH:33]=[CH:32][CH:31]=[N:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[F:23][C:22]([F:25])([F:24])[C:21]([OH:26])=[O:34].[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[C:16]([NH:20][CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[N:17][O:18][N:19]=2)[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

6

반응물 4

HCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58755133N-[4-[4-(3-Bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl]-2,2,2-trifluoroacetamide

생성물 1

HCID 674350304-(3-Bromo-4-fluorophenyl)-3-{4-[(pyridin-3-ylmethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one trifluoroacetate수율 6.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

A solution of N-{4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-2,2,2-trifluoroacetamide (50 mg, 0.11 mmol), nicotinyl alcohol (14 μL, 0.15 mmol), and triphenylphosphine (42 mg, 0.16 mmol) in tetrahydrofuran (0.35 mL) at 0° C. was treated with diisopropyl azodicarboxylate (34 μL, 0.17 mmol). The reaction mixture was stirred at 25° C. for 16 h and purified by preparative LCMS to give the desired product (4 mg, 6%). LCMS for C6H11BrFN6O3 (M+H)+: m/z=432.9, 434.9.

후처리

  1. custompurified by preparative LCMS

출처 및 근거

ORD 기록
ord-384f1284ccbf41b18c8c86f364eb230d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846726B2

연결된 노트

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