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Tetrahydro-4H-pyran-4-ol → tert-butyl 4-(2-{4-[2-chloro-7-(tetrahydro-2H-pyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(trifluoromethyl)phenoxy}ethyl)piperidine-1-carboxylate

HRID 522280
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HRID 522280 반응식
C(C=P(CCCC)(CCCC)CCCC)#N.[Cl:17][C:18]1[N:19]=[C:20]([C:27]2[CH:48]=[CH:47][C:30]([O:31][CH2:32][CH2:33][CH:34]3[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]3)=[C:29]([C:49]([F:52])([F:51])[F:50])[CH:28]=2)[C:21]2[CH:26]=[CH:25][NH:24][C:22]=2[N:23]=1.[O:53]1[CH2:58][CH2:57][CH:56](O)[CH2:55][CH2:54]1>C1(C)C=CC=CC=1>[Cl:17][C:18]1[N:19]=[C:20]([C:27]2[CH:48]=[CH:47][C:30]([O:31][CH2:32][CH2:33][CH:34]3[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:41])[CH2:36][CH2:35]3)=[C:29]([C:49]([F:50])([F:51])[F:52])[CH:28]=2)[C:21]2[CH:26]=[CH:25][N:24]([CH:56]3[CH2:57][CH2:58][O:53][CH2:54][CH2:55]3)[C:22]=2[N:23]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 74956Tetrahydro-4H-pyran-4-olHCID 4622928CyanomethylenetributylphosphoraneHCID 90065716tert-butyl 4-{2-[4-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidine-1-carboxylate

생성물 1

HCID 117899579tert-butyl 4-(2-{4-[2-chloro-7-(tetrahydro-2H-pyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(trifluoromethyl)phenoxy}ethyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 1140
Toluene
용매

실험 절차

Cyanomethylenetributylphosphorane (1.1 mL) was added to a mixture of tert-butyl 4-{2-[4-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidine-1-carboxylate (1.0 g), tetrahydro-2H-pyran-4-ol (0.36 mL), and toluene (30 mL) at room temperature in a nitrogen atmosphere, and the reaction mixture was stirred overnight while heating to reflux. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=67:33 to 33:67), whereby tert-butyl 4-(2-{4-[2-chloro-7-(tetrahydro-2H-pyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(trifluoromethyl)phenoxy}ethyl)piperidine-1-carboxylate (1.04 g) was obtained as a yellow amorphous material.

후처리

  1. temperaturewhile heating to reflux
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=67:33 to 33:67)

출처 및 근거

ORD 기록
ord-85753d2c72584525ae71437546368700
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09328118B2

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