1,2-Dichloroethane → HCID 24811988, compound

HRID 1945427Notes

Reaction equation

HRID 1945427 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][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]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][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:14])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 61055N-(3-Aminopropyl)morpholineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 668139HCID 668139, compound

Product 1

HCID 24811988HCID 24811988, compoundYield 20.6%

Reagents, catalysts & solvents 1

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

Procedure

3-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid (200 mg, 0.59 mmol) and N-(aminopropyl)morpholine (0.17 ml, 1.18 mmol) in DMF 3.0 mL was added EDC (168.7 mg, 0.88 mmol), HOBt (118.9 mg, 0.88 mmol) and DIPEA (0.15 ml, 0.88 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=15:1) to give 3-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-(3-morpholine-4-yl-propyl)-benzamide as a yellow solid (56.7 mg, 20% 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=15:1)

Sources & evidence

ORD record
ord-581760b45da6409a82bf6af30ab7155a
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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