Hydrochloric Acid → HCID 89783476, compound

HRID 1056204Notes

Reaction equation

HRID 1056204 reaction equation
C(OC([NH:8][CH2:9][C:10]1[NH:11][C:12]([C:20]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=2[N:22]=[C:23]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:24]([CH3:30])=[N:25]3)=[CH:13][C:14]=1[C:15]([O:17]CC)=[O:16])=O)(C)(C)C.[Li+].[OH-].O1CCOCC1.[ClH:44]>O>[ClH:44].[NH2:8][CH2:9][C:10]1[NH:11][C:12]([C:20]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=2[N:22]=[C:23]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:24]([CH3:30])=[N:25]3)=[CH:13][C:14]=1[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 89783943HCID 89783943, compound

Product 1

HCID 89783476HCID 89783476, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A glass microwave reaction vessel was charged with ethyl 2-(((tert-butoxycarbonyl)amino)methyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (334b) (0.27 g, 0.56 mmol), LiOH hydrated (0.12 g, 2.82 mmol), dioxane (3 mL), and water (1 mL). The reaction mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 110° C. for 3 h. The reaction mixture was acidified with HCl (1 N, 5 mL) and the orange solid obtained was filtered, washed with water, ether, and dried in a vacuum oven at 50° C. for 3 h. The orange solid was suspended in dioxane (2 mL), treated with HCl (2 mL of 4 N in dioxane), and stirred at RT for 4 h. The mixture was concentrated to half of its volume and the orange solid obtained was filtered, washed with ether and dried to give 2-(aminomethyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (334c), which was used as crude material and based on theoretical yield.

Workup

  1. customA glass microwave reaction vessel
  2. customthe orange solid obtained
  3. filtrationwas filtered
  4. washwashed with water, ether
  5. customdried in a vacuum oven at 50° C. for 3 h
  6. additiontreated with HCl (2 mL of 4 N in dioxane)
  7. stirringstirred at RT for 4 h
  8. concentrationThe mixture was concentrated to half of its volume
  9. customthe orange solid obtained
  10. filtrationwas filtered
  11. washwashed with ether
  12. customdried

Sources & evidence

ORD record
ord-bc5e46e042704819a03ecb57b6ec4dca
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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