1,2-Dichloroethane → HCID 58001341, compound

HRID 1945422Notes

Reaction equation

HRID 1945422 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].[NH2:23][CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=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:23][CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)=[O:14])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 773174-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 668139HCID 668139, compound

Product 1

HCID 58001341HCID 58001341, 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), 4-aminomethyl pyridine (0.024 ml, 0.24 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=30:1) to give 3-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-pyridine-4-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=30:1)

Sources & evidence

ORD record
ord-fd9c27e52dcc4648b3f9aae8d1d2ec4c
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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