Hydrochloric Acid → 2-[3-({3-[(2-Aminoethoxy)methyl]phenethyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide

HRID 2228779노트

반응식

HRID 2228779 반응식
Cl.[CH3:2][C:3]1[N:4]([CH2:31][C:32]([NH:34][CH2:35][C:36]2[CH:37]=[C:38]3[C:42](=[CH:43][CH:44]=2)[NH:41][CH:40]=[C:39]3[CH3:45])=[O:33])[C:5](=[O:30])[C:6]([NH:9][CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH:27]=[CH:28][CH:29]=2)[CH2:15][O:16][CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)=[N:7][CH:8]=1.[OH-].[Na+]>CO>[NH3:4].[NH2:19][CH2:18][CH2:17][O:16][CH2:15][C:14]1[CH:13]=[C:12]([CH:29]=[CH:28][CH:27]=1)[CH2:11][CH2:10][NH:9][C:6]1[C:5](=[O:30])[N:4]([CH2:31][C:32]([NH:34][CH2:35][C:36]2[CH:37]=[C:38]3[C:42](=[CH:43][CH:44]=2)[NH:41][CH:40]=[C:39]3[CH3:45])=[O:33])[C:3]([CH3:2])=[CH:8][N:7]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18470880tert-Butyl 2-{[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)benzyl]oxy}ethylcarbamate

생성물 2

HCID 222AmmoniaHCID 154914892-[3-({3-[(2-Aminoethoxy)methyl]phenethyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide수율 110.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Hydrochloric acid (10 ml, 6N, 60.0 mmol) was added to a solution of tert-butyl 2-{[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)benzyl]oxy}ethylcarbamate (preparation 108) (220 mg, 0.36 mmol) in methanol (10 ml), and the reaction stirred for an hour at room temperature. The mixture was basified using NaOH (1N) solution, and the mixture extracted with ethyl acetate (2×), and dichloromethane (1×). The combined organic extracts were dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1) to afford the title compound as a white solid, (100 mg, 55%).

후처리

  1. extractionthe mixture extracted with ethyl acetate (2×), and dichloromethane (1×)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-81ea0b2c975b46a287e0c657ee296bb6
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06417203B1

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