1,2-Dichloroethane → HCID 136337186, compound

HRID 1428867Notes

Reaction equation

HRID 1428867 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]([NH:26][C:27](OCC)=[O:28])=[N:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])=[CH:15][CH:14]=2)[CH:10]=1)=[O:5])[CH3:2].ClCCCl>[Ti](Cl)(Cl)(Cl)Cl.C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:26][C:27](=[O:28])[C:14]3[C:13](=[CH:18][CH:17]=[C:16]([C:19]([N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)=[O:20])[CH:15]=3)[N:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 136337187HCID 136337187, compound

Product 1

HCID 136337186HCID 136337186, compoundYield 2.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Titanium (IV) chloride (0.377 mL, 3.43 mmol) was carefully added to a solution of 1-{ethoxycarbonylamino-[4-(pyrrolidine-1-carbonyl)-phenylimino]-methyl}-1H-pyrazole-4-carboxylic acid ethyl ester (0.977 g, 2.29 mmol) and DCE (5.5 mL). The reaction mixture was heated to 100° C. for 2.5 h and was then cooled to room temperature and quenched with ethanol (10 mL). The resulting solution was concentrated and the residue was partitioned between DCM (30 mL) and water (30 mL). The two layers were filtered to remove a solid byproduct and then separated. The aqueous layer was washed with DCM (30 mL) and the combined organic layers were washed with brine (30 mL), dried (MgSO4), and concentrated. The residue was triturated with diethyl ether and then with ethanol to yield the titled compound (18 mg, 2.0% yield). MS (ESI/Cl): mass calcd. for C19H19N5O4, 381.1; m/z found, 382.1 [M+H]+.

Workup

  1. temperaturewas then cooled to room temperature
  2. customquenched with ethanol (10 mL)
  3. concentrationThe resulting solution was concentrated
  4. customthe residue was partitioned between DCM (30 mL) and water (30 mL)
  5. filtrationThe two layers were filtered
  6. customto remove a solid byproduct
  7. customseparated
  8. washThe aqueous layer was washed with DCM (30 mL)
  9. washthe combined organic layers were washed with brine (30 mL)
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-b71aaea4d0fb4192a348a06888d036cd
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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