Hydrochloric Acid → HCID 89783310, compound

HRID 1056348Notes

Reaction equation

HRID 1056348 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([C:19]1[NH:20][C:21]([C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[N:31]=[C:32]([NH:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C:33]([CH3:39])=[N:34]3)=[CH:22][C:23]=1[C:24]([O:26]CC)=[O:25])[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].O1CCOCC1.O.[ClH:54]>>[ClH:54].[NH2:11][CH:10]([C:19]1[NH:20][C:21]([C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[N:31]=[C:32]([NH:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C:33]([CH3:39])=[N:34]3)=[CH:22][C:23]=1[C:24]([OH:26])=[O:25])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 89783201HCID 89783201, compound

Product 1

HCID 89783310HCID 89783310, compound

Conditions

Temperature
100 °C

Procedure

To a 50-mL round bottomed flask was added ethyl 2-(2-(benzyloxy)-1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (468b) (0.97 g, 1.61 mmol), LiOH hydrated (0.34 g, 8.04 mmol), dioxane (10 mL), and water (10 mL). The reaction mixture was heated at 100° C. for 24 h and cooled to RT. The solvent was removed and the product used without further purification. The yellow solid obtained was suspended in HCl (10 mL, 4 N in dioxane) and the reaction mixture was stirred at RT for 2 h. The reaction mixture was concentrated under vacuum and the orange solid obtained was dried to give 2-(1-amino-2-(benzyloxy)ethyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (468c), which was used as crude material and based on theoretical yield.

Workup

  1. temperaturecooled to RT
  2. customThe solvent was removed
  3. customthe product used without further purification
  4. customThe yellow solid obtained
  5. concentrationThe reaction mixture was concentrated under vacuum
  6. customthe orange solid obtained
  7. customwas dried

Sources & evidence

ORD record
ord-a525c97ca0834f22ad5fe640fd1f041f
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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