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2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethynyl)-pyrazin-2-yl]-propionamide → 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethyl)-pyrazin-2-yl]-propionamide

HRID 719951
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HRID 719951 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:31][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([C:22]#[C:23][C:24]3([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:31][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH2:22][CH2:23][C:24]3([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]
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참가 물질

4

반응물 1

HCID 100072342(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethynyl)-pyrazin-2-yl]-propionamide

생성물 1

HCID 104822862(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethyl)-pyrazin-2-yl]-propionamide수율 84%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethynyl)-pyrazin-2-yl]-propionamide (prepared as in Example 50, 200 mg, 0.376 mmol) in methanol (30 mL) was treated with 10% palladium on activated carbon (39 mg). The reaction mixture was then placed on a Parr shaker under a hydrogen atomsphere of 50 psi for 4 h. The mixture was filtered, and solvents were concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethyl)-pyrazin-2-yl]-propionamide (169 mg, 84%) as a fluffy solid: (ES)+-HRMS m/e calcd for C26H34ClN3O5S (M+H)+ 536.1981, found 536.1988.

후처리

  1. filtrationThe mixture was filtered
  2. concentrationsolvents were concentrated in vacuo

출처 및 근거

ORD 기록
ord-a63ec33513b24e0ab5adff489d3c0e03
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07132425B2

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