1,2-Dichloroethane → HCID 18914199, compound

HRID 1292359Notes

Reaction equation

HRID 1292359 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH2:7][CH2:6][NH:5]1.[N:17]1[C:21]2[CH:22]=[CH:23][C:24]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([CH2:35][C:36](O)=[O:37])=[CH:31][CH:30]=3)=[O:27])=[CH:25][C:20]=2[NH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[N:17]1[C:21]2[CH:22]=[CH:23][C:24]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([CH2:35][C:36]([N:5]4[CH2:6][CH2:7][N:8]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=5[CH3:16])[CH2:9][CH:4]4[CH2:3][CH2:2][OH:1])=[O:37])=[CH:31][CH:30]=3)=[O:27])=[CH:25][C:20]=2[NH:19][CH:18]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 18914146HCID 18914146, compoundHCID 18914153HCID 18914153, compound

Product 1

HCID 18914199HCID 18914199, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(2-hydroxyethyl)-4-(2-methylphenyl)piperazine from Step 2 of Example 20 (0.20 g; 0.91 mmol), 4-(5-benzimidazolylcarbonylamino)phenylacetic acid (0.299 g; 1.00 mmol), HOBT (0.14 g; 1.0 mmol), and EDC (0.210 g; 1.09 mmol) in DMF (30 mL) was added DIEA (0.23 mL; 1.3 mmol). The reaction was stirred at ambient temperature for 18 h and the solvent was evaporated under reduced pressure. The residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic phase was separated and washed with saturated aqueous NaHCO3 and brine. The organic phase was dried (MgSO4), filtered, and the solvent was evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 95:5:0.5 CH2Cl2 : MeOH:NH4OH as eluant. Trituration in EtOAc gave the title compound as an amorphous solid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-9b798bd9baa0447f86920bd34c57df9b
Source dataset
uspto-grants-1998_05
Patent number
US05756504

Reaction notes

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