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(S)-(4-(3,4-Dichlorobenzyl)morpholin-2-YL)methanamine → n-{[(2s)-4-(3,4-Dichlorobenzyl)morpholin-2-yl]methyl}-2-[5-(4-fluorophenyl)-1,2,4oxadiazol-3-yl]acetamide

HRID 2212025
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HRID 2212025 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH2:13][C:14]([O:16]C)=O)[N:9]=2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:22][N:23]1[CH2:28][CH2:27][O:26][C@@H:25]([CH2:29][NH2:30])[CH2:24]1>CN1CCCC1=O.CO>[Cl:18][C:19]1[CH:20]=[C:21]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:22][N:23]1[CH2:28][CH2:27][O:26][C@@H:25]([CH2:29][NH:30][C:14](=[O:16])[CH2:13][C:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:12][N:11]=2)[CH2:24]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 10171585(S)-(4-(3,4-Dichlorobenzyl)morpholin-2-YL)methanamineHCID 85817174Methyl (5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]acetate

생성물 1

HCID 68880198n-{[(2s)-4-(3,4-Dichlorobenzyl)morpholin-2-yl]methyl}-2-[5-(4-fluorophenyl)-1,2,4oxadiazol-3-yl]acetamide수율 57.4%

시약·촉매·용매 2

HCID 13387N-methyl-2-pyrrolidone촉매
HCID 887
Methanol
용매
2회

실험 절차

A mixture of Intermediate 38 (0.024 g), Intermediate 9 (0.025 g), and 1-methyl-2-pyrrolidinone (1 drop) was subjected was subjected to irradiation in a 600 W microwave oven on full power for 4 mins. The reaction mixture was dissolved in methanol and applied to an ion exchange cartridge (2 g Isolute SCX, pre-conditioned with methanol). Elution with methanol (3 column volumes) followed 10% 0.880 ammonia in methanol (2 column volumes) and evaporation of the first basic fraction in vacuo gave the crude product. Purification by Biotage flash column chromatography on silica gel (8 g cartridge), eluting with 100:8:1 dichloromethane/ethanol/0.880 ammonia, gave the title compound as a white solid (0.025 g). LCMS (System A) Rf 2.85 min Mass Spectrum m/z 479, 481 [MH+]

후처리

  1. customwas subjected to irradiation in a 600 W microwave oven on full power for 4 mins
  2. washElution with methanol (3 column volumes)
  3. custom10% 0.880 ammonia in methanol (2 column volumes) and evaporation of the first basic fraction in vacuo
  4. customgave the crude product
  5. customPurification by Biotage flash column chromatography on silica gel (8 g cartridge)
  6. washeluting with 100:8:1 dichloromethane/ethanol/0.880 ammonia

출처 및 근거

ORD 기록
ord-b7237dedf4304fe6a8fdb8ecdd4c9e3c
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07101882B2

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