Pyridine → N-(7-(5-(ethylsulfonamido)-2-methylphenyl)isoquinolin-3-yl)cyclopropanecarboxamide

HRID 468736

반응식

HRID 468736 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1.N1C=CC=CC=1.[CH2:31]([S:33](Cl)(=[O:35])=[O:34])[CH3:32]>ClCCl>[CH2:31]([S:33]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]4[CH2:22][CH2:23]4)=[O:20])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1)(=[O:35])=[O:34])[CH3:32]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 67974803N-(7-(5-amino-2-methylphenyl)isoquinolin-3-yl)cyclopropanecarboxamide

생성물 1

HCID 67974962N-(7-(5-(ethylsulfonamido)-2-methylphenyl)isoquinolin-3-yl)cyclopropanecarboxamide수율 54.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N-(7-(5-amino-2-methylphenyl)isoquinolin-3-yl)cyclopropanecarboxamide (56.2 mg, 0.177 mmol) in methylene chloride (2.0 mL, 31 mmol) was added pyridine (0.20 mL, 2.5 mmol) and ethanesulfonyl chloride (23.0 uL, 0.243 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into dichloromethane, washed with water, dried over MgSO4, filtered, and evaporated in vacuo. The crude product was purified via reverse phase HPLC and lyophilized to yield 39.5 mg (54%) of N-(7-(5-(ethylsulfonamido)-2-methylphenyl)isoquinolin-3-yl)cyclopropanecarboxamide. LCMS (ESI): RT (min)=4.534, M+H=410.1, method=E; 1H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1H), 9.73 (s, 1H), 9.18 (s, 1H), 8.49 (s, 1H), 7.98 (s, 1H), 7.92 (d, J=8.6 Hz, 1H), 7.66 (dd, J=8.5, 1.6 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.18 (dd, J=8.1, 2.3 Hz, 1H), 7.15 (d, J=2.2 Hz, 1H), 3.10 (q, J=7.3 Hz, 2H), 2.21 (s, 3H), 2.12-2.04 (m, 1H), 1.21 (t, J=7.3 Hz, 3H), 0.84 (m, 4H).

후처리

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude product was purified via reverse phase HPLC

출처 및 근거

ORD 기록
ord-3d51669a54264a5ba998fb1cf2391c8e
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

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