Methyl isonipecotate → Methyl 1-(2-(5-(5-bromopyrimidin-2-ylamino)-2-fluorophenoxy)ethyl)piperidine-4-carboxylate

HRID 2067908

반응식

HRID 2067908 반응식
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[N:21]=[CH:20][C:19]([Br:22])=[CH:18][N:17]=2)[CH:12]=[CH:11][C:10]=1[F:23])(=O)=O.[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH3:33])=[O:31])[CH2:26][CH2:25]1>CN1C(=O)CCC1.O>[Br:22][C:19]1[CH:20]=[N:21][C:16]([NH:15][C:13]2[CH:12]=[CH:11][C:10]([F:23])=[C:9]([CH:14]=2)[O:8][CH2:7][CH2:6][N:24]2[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH3:33])=[O:31])[CH2:26][CH2:25]2)=[N:17][CH:18]=1

참가 물질

5

반응물 2

HCID 424914Methyl isonipecotateHCID 866601232-(5-(5-Bromopyrimidin-2-ylamino)-2-fluorophenoxy)ethyl methanesulfonate

생성물 1

HCID 58542307Methyl 1-(2-(5-(5-bromopyrimidin-2-ylamino)-2-fluorophenoxy)ethyl)piperidine-4-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
90 °C

실험 절차

2-(5-(5-bromopyrimidin-2-ylamino)-2-fluorophenoxy)ethyl methanesulfonate 46b (0.24 mmol) and methyl piperidine-4-carboxylate (0.48 mmol) are dissolved in NMP (2 mL) and heated to 90° C. for 3 h. The reaction mixture is cooled to rt and diluted with water and extracted with EtOAc (2×30 mL). The organic layer is washed with water, brine, dried over sodium sulfate, and concentrated to dryness. The crude product is purified by short SiO2 chromatography using DCM:hexane=9:1 as eluant to yield methyl 1-(2-(5-(5-bromopyrimidin-2-ylamino)-2-fluorophenoxy)ethyl)piperidine-4-carboxylate 47 as light brown solid. MS (m/z) (M+1)+: 454.1.

후처리

  1. temperatureThe reaction mixture is cooled to rt
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe organic layer is washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude product is purified by short SiO2 chromatography

출처 및 근거

ORD 기록
ord-5eacd9c8f44141448122ab8b1c12f878
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293757B2

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