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2,2,2-Cryptand → N-[[3-fluoro-4-(2-fluoroethoxymethyl)phenyl]methyl]-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 929372
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인쇄 미리보기

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HRID 929372 반응식
CC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]([C:26]3[C:27]([CH3:36])=[N:28][C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][N:30]=4)=[O:25])=[CH:18][C:17]=2[F:37])(=O)=O)=CC=1.C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.[F-:64].[K+]>CC#N.O>[F:37][C:17]1[CH:18]=[C:19]([CH2:22][NH:23][C:24]([C:26]2[C:27]([CH3:36])=[N:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][N:30]=3)=[O:25])[CH:20]=[CH:21][C:16]=1[CH2:15][O:14][CH2:13][CH2:12][F:64]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 728012,2,2-CryptandHCID 522689Potassium FluorideHCID 896472142-[[2-Fluoro-4-[[(2-methyl-1,8-naphthyridine-3-carbonyl)amino]methyl]phenyl]methoxy]ethyl 4-methylbenzenesulfonate

생성물 1

HCID 78122360N-[[3-fluoro-4-(2-fluoroethoxymethyl)phenyl]methyl]-2-methyl-1,8-naphthyridine-3-carboxamide

시약·촉매·용매 2

HCID 962Water용매
HCID 6342Acetonitrile용매

실험 절차

A flask with a solution of 19 mg 2-[[2-fluoro-4-[[(2-methyl-1,8-naphthyridine-3-carbonyl)amino]methyl]phenyl]methoxy]ethyl 4-methylbenzenesulfonate (0.036 mmol), 26 mg Kryptofix 222 (4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]-hexacosane) (0.069 mmol) and 4 mg KF (0.069 mmol) in 1.0 ml dry MeCN was added to a preheated oil bath and heated at 90 C for 30 min. The reaction mixture was cooled to room temperature and diluted with water. The mixture was extracted twice with EtOAc. The combined organic phases were washed with brine, dried (MgSO4) and concentrated. Flash chromatography gave 9.6 mg (72%).

후처리

  1. temperatureheated at 90 C for 30 min
  2. extractionThe mixture was extracted twice with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customFlash chromatography gave 9.6 mg (72%)

출처 및 근거

ORD 기록
ord-ed5f4861cf834ccaa64a34d401950b2e
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09295738B2

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