Hydrochloric Acid → HCID 89783230, compound

HRID 1056192Notes

Reaction equation

HRID 1056192 reaction equation
C(OC([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:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:25]([CH3:31])=[N:26]3)=[CH:14][C:15]=1[C:16]([O:18]CC)=[O:17])[CH3:10])=O)(C)(C)C.[Li+].[OH-].[ClH:39]>O1CCOCC1.O>[ClH:39].[NH2:8][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:32][C:33]([CH3:34])([CH3:36])[CH3:35])[C:25]([CH3:31])=[N:26]3)=[CH:14][C:15]=1[C:16]([OH:18])=[O:17])[CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89783604ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 89783230HCID 89783230, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (326b) (6.30 g, 12.71 mmol) and LiOH hydrated (2.67 g, 63.6 mmol) in dioxane (24 mL) and water (24 mL) was heated in an oil bath at 100° C. for 10 h. The reaction mixture was concentrated to half of its volume. The remaining mixture was lyophilized for 24 h to give a yellow solid. The yellow solid suspended in 15 mL of dioxane at 0° C. was treated with 35 mL of 4 N HCl in dioxane. The resulting orange mixture was stirred at RT for 2 h. The mixture was concentrated to half of its volume. The insoluble solid was filtered, rinsed with 2×10 mL of ether. The filtrate was discarded. The orange solid was dried in a vacuum oven at 40° C. for 1 h to give 2-(1-aminoethyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (326c), which was used as crude material and based on theoretical yield. m/z (ESI, +ve) 368.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated to half of its volume
  2. customto give a yellow solid
  3. concentrationThe mixture was concentrated to half of its volume
  4. filtrationThe insoluble solid was filtered
  5. washrinsed with 2×10 mL of ether
  6. customThe orange solid was dried in a vacuum oven at 40° C. for 1 h

Sources & evidence

ORD record
ord-453d64db27144d58922491ae669ec033
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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