1,2-Dichloroethane → HCID 58870811, compound

HRID 1927606Notes

Reaction equation

HRID 1927606 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=2[Cl:24])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:26][C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](O)=[O:30].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:25])[CH:4]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=3[CH3:26])=[CH:19][C:18]=2[Cl:24])[CH2:15][CH2:16]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 83732-Methylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 58870754HCID 58870754, compound

Product 1

HCID 58870811HCID 58870811, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of [4-(4-amino-2-chloro-phenyl)-piperazin-1-yl]-phenyl-acetic acid methyl ester (25 mg, 0.07 mmol), 2-methyl-benzoic acid (19 mg, 0.14 mmol), EDC (27 mg, 0.14 mmol), and HOBt (19 mg, 0.14 mmol) in DCM (5 mL) was added N-methylmorpholine (77 μL, 0.70 mmol). After 16 h, the mixture was diluted with satd. aq. NaHCO3 (10 mL) and extracted with DCM (75 mL). The organic fraction was washed with brine, dried (Na2SO4), and concentrated. The residue was purified by SiO2 column chromatography to provide the title compound (16 mg, 46%). MS (ESI): mass calcd. for C27H28ClN3O3, 477.18. m/z found, 478.4 [M+H]+. 1H NMR (CDCl3): 7.76-7.60 (m, 1H), 7.51-7.23 (m, 8H), 7.22-7.15 (m, 2H), 6.97 (d, J=8.7, 1H), 3.66 (s, 3H), 3.15-2.93 (m, 5H), 2.85-2.49 (m, 4H), 2.42 (s, 3H).

Workup

  1. additionthe mixture was diluted with satd
  2. extractionaq. NaHCO3 (10 mL) and extracted with DCM (75 mL)
  3. washThe organic fraction was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-590bfb6a47a24d58aafe2d33527b689e
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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