Hydrochloric Acid → HCID 59292935, compound

HRID 43054Notes

Reaction equation

HRID 43054 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[C:24]4[N:25]=[CH:26][CH:27]=[N:28][C:29]=4[C:30]([C:33]4[C:38]([Cl:39])=[C:37]([O:40][CH3:41])[CH:36]=[C:35]([O:42][CH3:43])[C:34]=4[Cl:44])=[CH:31][CH:32]=3)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1.C(Cl)Cl.O>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]3[C:24]4[N:25]=[CH:26][CH:27]=[N:28][C:29]=4[C:30]([C:33]4[C:38]([Cl:39])=[C:37]([O:40][CH3:41])[CH:36]=[C:35]([O:42][CH3:43])[C:34]=4[Cl:44])=[CH:31][CH:32]=3)=[O:22])=[CH:18][CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 866411394-(4-{[8-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonyl]-amino}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59292935HCID 59292935, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(4-{[8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonyl]-amino}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (Step 8.1) (137 mg, 0.22 mmol) and a 4 N solution of HCl in dioxane (5 mL) was stirred for 1 h at rt. The reaction mixture was diluted with DCM and H2O. The aqueous layer was separated and extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was triturated in Et2O to afford 95 mg of the title compound as a red solid: ESI-MS: 537.9/539.9 [M+H]+; tR=4.01 min (System 1).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with DCM
  3. washThe organic phase was washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated in Et2O

Sources & evidence

ORD record
ord-2f385962300641b9b2684ff96426fc9e
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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