1,2-Dichloroethane → HCID 24811884, compound

HRID 1945424Notes

Reaction equation

HRID 1945424 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)=[O:7].NCC[N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(Cl)CCl.C1C=CC2N(O)N=[N:42][C:40]=2C=1.CCN(C(C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH:42][CH2:40][C:30]1[CH:31]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:14])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 33944N-(2-Aminoethyl)piperidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 668139HCID 668139, compound

Product 1

HCID 24811884HCID 24811884, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolSolvent

Procedure

To solution of 3-[2-(2,4-dichloro-phenoxy)acetylamino]-benzoic acid (68 mg, 0.2 mmol), 1-(2-aminoethyl)-piperidine (0.043 ml, 0.3 mmol) in DMF 3.0 mL was added EDC (57.5 mg, 0.3 mmol), HOBt (40.6 mg, 0.3 mmol) and DIPEA (0.052 ml, 0.3 mmol). Reaction mixture was stirred at room temperature, and separated by EtoAC and brine. The organic phase was dried (MgSO4 anh) and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=20:1) to give 3-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-pyridine-3-ylmethyl-benzamide as a white solid (60.6 mg, 70% yield).

Workup

  1. customReaction mixture
  2. customseparated by EtoAC and brine
  3. dry with materialThe organic phase was dried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=20:1)

Sources & evidence

ORD record
ord-4a0a02845fb14484a0e9586b2963908b
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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