Water → ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-((1-hydroxy-2-methylpropan-2-yl)amino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate

HRID 1056157Notes

Reaction equation

HRID 1056157 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[NH:12][C:13]([C:21]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:22]=2[N:23]=[C:24](F)[C:25]([CH3:31])=[N:26]3)=[CH:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:33][C:34]([CH3:38])([CH3:37])[CH2:35][OH:36].O.CCOC(C)=O>CS(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[NH:12][C:13]([C:21]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:22]=2[N:23]=[C:24]([NH:33][C:34]([CH3:38])([CH3:37])[CH2:35][OH:36])[C:25]([CH3:31])=[N:26]3)=[CH:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 118072-Amino-2-methyl-1-propanolHCID 89783450HCID 89783450, compound

Product 1

HCID 89783773ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-((1-hydroxy-2-methylpropan-2-yl)amino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (302b) (250 mg, 0.57 mmol) and 2-amino-2-methyl-1-propanol (Sigma-Aldrich) (0.11 mL, 1.13 mmol) in DMSO (2 mL) was heated at 70° C. for 18 h. The reaction mixture was cooled to RT and water and EtOAc was added. The layers were separated and the aq. layer was extracted with EtOAc (2×). The combined organic layers were washed with water and brine and dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by chromatography (0-100% EtOAc in hexanes) to provide ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(34(1-hydroxy-2-methylpropan-2-yl)amino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (302c) (208 mg, 0.41 mmol, 72% yield) as a yellow oil. m/z (ESI, +ve) 512.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customThe layers were separated
  3. extractionthe aq. layer was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8d89a6a8d968419a8e00e2bea07daf5d
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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