Hydrochloric Acid → HCID 89783703, compound

HRID 1056261Notes

Reaction equation

HRID 1056261 reaction equation
C(OC([NH:8][C:9]1([C:12]2[NH:13][C:14]([C:22]3[CH:31]=[CH:30][CH:29]=[C:28]4[C:23]=3[N:24]=[C:25]([NH:33][CH2:34][C:35]([F:38])([F:37])[F:36])[C:26]([CH3:32])=[N:27]4)=[CH:15][C:16]=2[C:17]([O:19]CC)=[O:18])[CH2:11][CH2:10]1)=O)(C)(C)C.[ClH:39]>O1CCOCC1.O>[ClH:39].[NH2:8][C:9]1([C:12]2[NH:13][C:14]([C:22]3[CH:31]=[CH:30][CH:29]=[C:28]4[C:23]=3[N:24]=[C:25]([NH:33][CH2:34][C:35]([F:36])([F:38])[F:37])[C:26]([CH3:32])=[N:27]4)=[CH:15][C:16]=2[C:17]([OH:19])=[O:18])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89783881HCID 89783881, compound

Product 1

HCID 89783703HCID 89783703, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylate (381a, 970 mg, 1.81 mmol) and LiOH monohydrate (381 mg, 9.09 mmol) in dioxane (8.0 mL) and water (4.00 mL) was heated at 110° C. for 5 h. It was concentrated to dryness and the remaining solid was treated with 4.0 M HCl solution in 1,4-dioxane (11.36 mL, 45.5 mmol) at RT and stirred for 30 min. The reaction mixture was concentrated to give 2-(1-aminocyclopropyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (381b) as a red-orange solid. It was used in the subsequent step without further purification assuming quantitative yield. m/z (ESI, +ve ion) 406.1 (M−35)+.

Workup

  1. concentrationIt was concentrated to dryness
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-0f485601444142e6b795bfbe5f632ec2
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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