홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium hydride → 4-[4-(4-Methanesulfonyl-phenoxy)-3-methyl-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester

HRID 1931631
노트
인쇄 미리보기

반응식

HRID 1931631 반응식
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5].[CH:14]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:30]3=[N:31][CH:32]=[N:33][C:34](Cl)=[C:29]3[C:28]([CH3:36])=[N:27]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])[CH3:15].[Cl-].[NH4+]>CN(C)C=O>[CH:14]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:30]3=[N:31][CH:32]=[N:33][C:34]([O:13][C:10]4[CH:11]=[CH:12][C:7]([S:4]([CH3:3])(=[O:5])=[O:6])=[CH:8][CH:9]=4)=[C:29]3[C:28]([CH3:36])=[N:27]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])[CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1233504-(Methylsulfonyl)phenolHCID 579649474-(4-Chloro-3-methyl-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylic acid isopropyl ester2회

생성물 1

HCID 579650154-[4-(4-Methanesulfonyl-phenoxy)-3-methyl-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (60% dispersion in mineral oil; 7 mg, 0.18 mmol) was added to a solution of 4-(methylsulfonyl)phenol (20 mg, 0.12 mmol) in dimethylformamide (1 mL) and the mixture was stirred at room temperature for 15 min. A solution of 4-(4-chloro-3-methyl-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester (Intermediate 21; 40 mg, 0.12 mmol) in dimethylformamide (1 mL) was added, and the reaction mixture was allowed to stir at room temperature overnight. Saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate (3×25 mL). The organic layer was washed with water (3 times) and brine, dried (sodium sulfate), filtered, evaporated and purified on a flash silica column (20 mm×3″) eluting with 75-80% ethyl acetate/hexanes to give 4-[4-(4-methanesulfonyl-phenoxy)-3-methyl-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester (38 mg, 68%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.20 (d, 6H, J=6.3 Hz), 1.93-2.02 (m, 4H), 2.62 (s, 3H), 3.03-3.09 (m, 2H), 3.32 (s, 3H), 4.08-4.12 (m, 2H), 4.77-4.81 (m, 1H), 4.85-4.95 (m, 1H), 7.59-7.62 (m, 2H), 8.01-8.04 (m, 2H), 8.46 (s, 1H). Mass spectrum (ES) MH+=474.

후처리

  1. stirringto stir at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate (3×25 mL)
  3. washThe organic layer was washed with water (3 times) and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. custompurified on a flash silica column (20 mm×3″)
  8. washeluting with 75-80% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-136fc32cf36045d1a7cb5393305014c2
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08188098B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트