1,2-Dichloroethane → HCID 58001325, compound

HRID 1945449Notes

Reaction equation

HRID 1945449 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][N:17]=1)[C:12]([OH:14])=O)=[O:7].[N:23]1([CH2:29][CH2:30][NH2:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)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][N:17]=1)[C:12]([NH:31][CH2:30][CH2:29][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:14])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 33944N-(2-Aminoethyl)piperidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 580013332-[2-(2,4-Dichloro-phenoxy)acetylamino]-isonicotinic acid

Product 1

HCID 58001325HCID 58001325, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-isonicotinic acid (80.0 mg, 0.24 mmol), 2-piperidine-1-yl-ethylamine (46.2 mg, 0.05 ml, 0.36 mmol), EDC (69.0 mg, 0.36 mmol) and HOBt (48.7 mg, 0.36 mmol) in DMF 4 ml was added DIPEA (46.5 mg, 0.06 ml, 0.36 mmol), and stirred. Reaction mixture was then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by preparative-TLC (n-Hexane:EtoAC:MeOH=6:3:1) to afford 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-(2-piperidine-1-yl-ethyl)-isonicotinamide as a yellow solid (14.3 mg, 13.3% yield).

Workup

  1. customReaction mixture
  2. customwas then partitioned between ethyl acetate and 10% HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative-TLC (n-Hexane:EtoAC:MeOH=6:3:1)

Sources & evidence

ORD record
ord-29475b4f34884596bd3926b30b9bcec2
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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