1,2-Dichloroethane → 5-chloro-1-(3-chlorobenzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]ethyl}-amide

HRID 365473Notes

Reaction equation

HRID 365473 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]([OH:19])=O)[C:5](=[O:16])[N:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[CH:7]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:34]([C:36]1[CH:50]=[CH:49][C:39]([CH2:40][NH:41][CH2:42][CH2:43][C:44]2[N:48]=CNC=2)=[CH:38][CH:37]=1)#[N:35].[CH3:51][N:52]1CCOC[CH2:53]1>CN(C=O)C>[C:34]([C:36]1[CH:37]=[CH:38][C:39]([CH2:40][N:41]2[C:42]([CH2:43][CH2:44][NH:48][C:17]([C:4]3[C:5](=[O:16])[N:6]([CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=4)[CH:7]=[C:2]([Cl:1])[CH:3]=3)=[O:19])=[CH:53][N:52]=[CH:51]2)=[CH:49][CH:50]=1)#[N:35]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 37808715-Chloro-1-(3-chlorobenzyl)-2-oxo-1,2-dihydro-3-pyridinecarboxylic acidHCID 178509848HCID 178509848, compound

Product 1

HCID 543120085-chloro-1-(3-chlorobenzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]ethyl}-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-1-(3-chlorobenzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid (0.10 g, 0.335 mmol) was dissolved in DMF (10 mL) and treated with EDC (0.077 g, 0.402 mmol), HOBT (0.054 g, 0.402 mmol), 4-cyanobenzyl histamine (0.079 g, 0.352 mmol) and NMM (0.11 mL, 1.00 mmol) and stirred at ambient temperature for 18 hr. The reaction mixture was concentrated to remove the DMF, then partitioned between EtOAc and aq saturated NaHCO3 solution, the organic layer separated, washed with brine and dried (MgSO4). The title compound was obtained upon purification by RP HPLC on a PrepPak column eluting with an acetonitrile/H2O/TFA gradient followed by neutralization with NaHCO3 and extraction.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the DMF
  3. custompartitioned between EtOAc and aq saturated NaHCO3 solution
  4. customthe organic layer separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-edb5ca1800d34bb0b19648c103b68fd9
Source dataset
uspto-grants-2000_10
Patent number
US06127390

Reaction notes

Loading…