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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0

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Sodium hydride → (1R,2S)-2-(4-chlorophenyl)-1'-((tetrahydro-2 H-pyran-4-yl)methyl)spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805321

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HRID 1805321 반응식

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]3=[O:19])[CH2:9]2)=[CH:4][CH:3]=1.ClC1C=[CH:25][C:24]([C@H:27]2[C@@:29]3(C4C(=CC=CC=4)N[C:30]3=[O:38])[CH2:28]2)=CC=1.[H-].[Na+].BrCC1CCOCC1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C@@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:28][CH:27]4[CH2:29][CH2:30][O:38][CH2:25][CH2:24]4)[C:11]3=[O:19])[CH2:9]2)=[CH:6][CH:7]=1

참가 물질 실험 절차 후처리 출처 및 근거 반응 노트

참가 물질

6

반응물 4

HCID 24758Sodium hydride

HCID 27732864-(Bromomethyl)oxane

HCID 58305306(1R,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

HCID 672320902-(4-Chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

생성물 1

HCID 53244943(1R,2S)-2-(4-chlorophenyl)-1'-((tetrahydro-2 H-pyran-4-yl)methyl)spiro[cyclopropane-1,3'-indolin]-2'-one수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Racemic (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one and (1R,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one (270 mg, 1.0 mmol, 1.0 equiv.) were added to a stirred solution of sodium hydride (60%, 60 mg, 1.5 mmol) in 5 mL of DMF under argon atmosphere at 0° C. After stirring for 1 hour, 4-bromomethyl-tetrahydropyran (215 mg, 1.2 mmol) was added. The reaction mixture was stirred for 14 hours at room temperature. The crude product was purified by HPLC to give the title compound as a white solid (258 mg, 70%). LC/MS m/e calcd. for C22H22ClNO2: 367, observed (M+H)+: 368.2 1H NMR (400 MHz, MeOD-d4) δppm 1.39-1.55 (m, 2 H) 1.65 (dd, J=13.14, 1.77 Hz, 2 H) 2.11-2.25 (m, 3 H) 3.22 (t, J=8.46 Hz, 1 H) 3.37-3.47 (m, 2 H) 3.79 (d, J=7.33 Hz, 2 H) 3.94-4.04 (m, 2 H) 6.09 (d, J=7.58 Hz, 1 H) 6.76 (t, J=7.58 Hz, 1 H) 7.11 (d, J=7.83 Hz, 1 H) 7.17-7.25 (m, 3 H) 7.33 (d, J=8.34 Hz, 2 H). MS calcd. For C22H22ClNO2 367, obsd. (ESI+) [(M+H)+] 368.

후처리

stirringThe reaction mixture was stirred for 14 hours at room temperature
customThe crude product was purified by HPLC

출처 및 근거

ORD 기록: ord-0cc18b52a186493a843a0a1711b0a8c8
출처 데이터셋: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08354443B2

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