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Methoxymethyl-triphenylphosphonium chloride → N-(3-Chloro-4-fluorophenyl)-4-[(E)-2-methoxyvinyl]-1,2,5-oxadiazole-3-carboxamide N-(3-chloro-4-fluorophenyl)-4-[(Z)-2-methoxyvinyl]-1,2,5-oxadiazole-3-carboxamide

HRID 1845781
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HRID 1845781 반응식
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].[Cl:30][C:31]1[CH:32]=[C:33]([NH:38][C:39]([C:41]2[C:45]([CH:46]=O)=[N:44][O:43][N:42]=2)=[O:40])[CH:34]=[CH:35][C:36]=1[F:37]>C1(C)C=CC=CC=1.C1COCC1>[Cl:30][C:31]1[CH:32]=[C:33]([NH:38][C:39]([C:41]2[C:45](/[CH:46]=[CH:2]\[O:3][CH3:4])=[N:44][O:43][N:42]=2)=[O:40])[CH:34]=[CH:35][C:36]=1[F:37].[Cl:30][C:31]1[CH:32]=[C:33]([NH:38][C:39]([C:41]2[C:45](/[CH:46]=[CH:2]/[O:3][CH3:4])=[N:44][O:43][N:42]=2)=[O:40])[CH:34]=[CH:35][C:36]=1[F:37]
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참가 물질

6

반응물 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23676156Sodium t-butoxideHCID 58941813HCID 58941813, 화합물

생성물 1

HCID 86689417N-(3-Chloro-4-fluorophenyl)-4-[(E)-2-methoxyvinyl]-1,2,5-oxadiazole-3-carboxamide N-(3-chloro-4-fluorophenyl)-4-[(Z)-2-methoxyvinyl]-1,2,5-oxadiazole-3-carboxamide

시약·촉매·용매 2

HCID 1140Toluene
용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (methoxymethyl)(triphenyl)phosphonium chloride (23.0 g, 66.0 mmol) in toluene (183 mL) was added sodium tert-butoxide (6.60 g, 0.066 mol) at rt under an atmosphere of nitrogen. After stirring for 30 min, a solution of N-(3-chloro-4-fluorophenyl)-4-formyl-1,2,5-oxadiazole-3-carboxamide (7.6 g, 28 mmol) in THF (18 mL) was cannulated into reaction flask. The resulting solution was stirred at rt for 1 h. The reaction was quenched with 1 N HCl and diluted with ethyl acetate and the aqueous layer was extracted with ethyl acetate once. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified with silica gel chromatography (20% ethyl acetate/Hex) to give product (2.0 g 24%, E isomer, 2.6 g, 31%, Z isomer) as white solids. Z isomer: 1H NMR (400 MHz, CDCl3): δ□ 8.54 (s, 1 H) 7.87 (dd, J=6.4, 2.7 Hz, 1 H), 7.42 (m, 1 H), 7.16 (t, J=8.5 Hz, 1 H), 6.66 (d, J=6.6 Hz, 1 H), 6.03 (d, J=6.6 Hz, 1 H), 3.97 (s, 3 H). MF=C12H10ClFN3O3; LCMS for C12H10ClFN3O3(M+H)+: m/z=298.0.

후처리

  1. stirringThe resulting solution was stirred at rt for 1 h
  2. customThe reaction was quenched with 1 N HCl
  3. additiondiluted with ethyl acetate
  4. extractionthe aqueous layer was extracted with ethyl acetate once
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified with silica gel chromatography (20% ethyl acetate/Hex)
  10. customto give product (2.0 g 24%, E isomer, 2.6 g, 31%, Z isomer) as white solids

출처 및 근거

ORD 기록
ord-ba15b76d933c43fb8333aa7de07839f0
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08951536B2

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