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 567849ノート

反応式

HRID 567849 の反応式
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

参加物

6

反応物 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

生成物 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]acetamide収率 110.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7b032c7d867a40dbbd84a759ae7fde39
出典データセット
uspto-grants-2001_01
特許番号
US06180627B2

反応ノート

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