1,2-Dichloroethane → HCID 25216688, compound

HRID 910684Notes

Reaction equation

HRID 910684 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:15]=[C:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26](O)=[O:27])=[CH:22][CH:21]=4)[CH:17]=[CH:18][CH:19]=3)[CH:9]=2)[CH2:4][CH2:3]1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:15]=[C:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[O:27])=[CH:22][CH:21]=4)[CH:17]=[CH:18][CH:19]=3)[CH:9]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 25216687HCID 25216687, compound

Product 1

HCID 25216688HCID 25216688, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3′-[4-(4-methyl-piperazin-1-yl)-pyridin-2-yl]-biphenyl-4-carboxylic acid (30 mg, 0.08 mmol) in DMF (2 mL) was added morpholine (16 mg, 0.16 mmol), EDC (20 mg, 0.1 mmol), and Et3N (10 mg, 0.1 mmol). The resulting mixture was stirred at room temperature overnight, and then was poured into water and extracted with CH2Cl2. The organic layer was washed with 1 N HCl, 2 M aqueous Na2CO3, dried, and concentrated, and the resulting residue was purified by preparative TLC (MeOH/CH2Cl2) to yield the title compound as a white solid.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with 1 N HCl, 2 M aqueous Na2CO3
  3. customdried
  4. concentrationconcentrated
  5. customthe resulting residue was purified by preparative TLC (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-515179af42a6422eaf22448095d43154
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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