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 567849Notes

Reaction equation

HRID 567849 reaction equation
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

Participants

6

Reactant 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

Product 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]acetamideYield 110.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-7b032c7d867a40dbbd84a759ae7fde39
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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