1,2-Dichloroethane → HCID 68931000, compound

HRID 32111Notes

Reaction equation

HRID 32111 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][CH:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][C:15]([OH:17])=O)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:24][N:25]([CH3:40])[CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH:35]([NH2:39])[CH2:34][CH2:33][CH2:32]2.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][CH:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][C:15]([NH:39][CH:35]2[C:36]3[C:31](=[CH:30][C:29]([O:28][CH2:27][CH2:26][N:25]([CH3:40])[CH3:24])=[CH:38][CH:37]=3)[CH2:32][CH2:33][CH2:34]2)=[O:17])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 230026233-(3,4-Dichloro-benzenesulfonylamino)-3-phenyl-propionic acidHCID 58841411HCID 58841411, compound

Product 1

HCID 68931000HCID 68931000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 20 mL vial equipped with stirring was added 3-(3,4-dichloro-benzenesulfonylamino)-3-phenyl-propionic acid (128 mg, 0.34 mmol), 6-(2-dimethylamino-ethoxy)-1,2,3,4-tetrahydro-naphthalen-1-ylamine (40 mg, 0.17 mmol), EDC (Aldrich, 49 mg, 0.26 mmol), HOBt (Aldrich, 23 mg, 0.17 mmol), and CH2Cl2 (1 mL). The reaction was stirred at RT overnight and diluted with CH2Cl2 (50 mL). The organic phase was washed with saturated NaHCO3, and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel chromatography (4%-6% MeOH—CH2Cl2) to afford the title compound as a white solid. MS (ESI): 590 (M+H)+.

Workup

  1. customTo a 20 mL vial equipped
  2. stirringThe reaction was stirred at RT overnight
  3. washThe organic phase was washed with saturated NaHCO3, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by silica gel chromatography (4%-6% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-d1614438b5d2407aa6729a6657eec23b
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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