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Water → N-[(3-Fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-(oxetan-3-yloxy)-pyridine-3-carboxylic acid amide

HRID 1039777
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HRID 1039777 반응식
[OH:1][CH:2]1[CH2:5][O:4][CH2:3]1.CC([O-])(C)C.[K+].Cl[C:13]1[C:18]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)=[O:20])=[C:17]([CH3:30])[CH:16]=[C:15]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[N:14]=1.O>C1COCC1>[F:29][C:25]1[CH:24]=[C:23]([CH2:22][NH:21][C:19]([C:18]2[C:13]([O:1][CH:2]3[CH2:5][O:4][CH2:3]3)=[N:14][C:15]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:16][C:17]=2[CH3:30])=[O:20])[CH:28]=[CH:27][CH:26]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 9942117Oxetan-3-olHCID 23665647Potassium tert-butoxideHCID 866643172-chloro-N-[(3-fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide

생성물 1

HCID 67288627N-[(3-Fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-(oxetan-3-yloxy)-pyridine-3-carboxylic acid amide수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
50 °C

실험 절차

A solution of 209 mg (2.82 mmol) 3-hydroxy-oxetane in THF (6 ml) was treated with 316 mg (2.81 mmol) KOtBu and was heated at 50° C. for 15 min. After cooling to RT a solution of 205 mg (0.56 mmol) 2-chloro-N-[(3-fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide (synthesis is described in section a) of example 9) in THF (3 ml) was added and the mixture was heated at 80° C. for 8 h. The mixture was then poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 7:3) provided 190 mg (0.47 mmol, 84%) N-[(3-Fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-(oxetan-3-yloxy)-pyridine-3-carboxylic acid amide (example 317). [M+H]+ 402.2.

후처리

  1. customsynthesis
  2. additionwas added
  3. temperaturethe mixture was heated at 80° C. for 8 h
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by CC (hexane/EtOAc 7:3)

출처 및 근거

ORD 기록
ord-d7b4aa55d9154d2ab1cc0fd39cc350c2
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552200B2

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