1,2-Dichloroethane → 4-(3-Chlorobenzyloxy)-6-methoxycarbonyl-pyridine-2-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]ethyl}-amide

HRID 365474Notes

Reaction equation

HRID 365474 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]=[C:9]([C:16]([OH:18])=O)[CH:8]=1.C(Cl)CCl.[CH:26]1C=CC2N(O)N=NC=2C=1.[C:36]([C:38]1[CH:52]=[CH:51][C:41]([CH2:42][NH:43][CH2:44][CH2:45][C:46]2[N:50]=CNC=2)=[CH:40][CH:39]=1)#[N:37].[CH3:53][N:54]1CCOC[CH2:55]1>CN(C=O)C>[C:36]([C:38]1[CH:39]=[CH:40][C:41]([CH2:42][N:43]2[C:44]([CH2:45][CH2:46][NH:50][C:16]([C:9]3[CH:8]=[C:7]([O:6][CH2:5][C:4]4[CH:19]=[CH:20][CH:21]=[C:2]([Cl:1])[CH:3]=4)[CH:12]=[C:11]([C:13]([O:15][CH3:26])=[O:14])[N:10]=3)=[O:18])=[CH:55][N:54]=[CH:53]2)=[CH:51][CH:52]=1)#[N:37]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 232920514-(3-Chlorobenzyloxy)-pyridine-2,6-dicarboxylic acidHCID 178509848HCID 178509848, compound

Product 1

HCID 543235734-(3-Chlorobenzyloxy)-6-methoxycarbonyl-pyridine-2-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]ethyl}-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mono methyl ester of 4-(3-chlorobenzyloxy)-pyridine-2,6-dicarboxylic acid (0.236 g, 0.622 mmol) was dissolved in DMF (2 mL) and treated with EDC (0.125 g, 0.653 mmol), HOBT (0.080 g, 0.59 mmol), 4-cyanobenzylhistamine (0.141 g, 0.622 mmol) and the pH adjusted to 7.5 with NMM. After stirring overnight at ambient temperature, the reaction mixture was concentrated to remove the DMF, the residue partitioned between EtOAc and aq saturated NaHCO3 solution, the organic layer separated, washed with brine and dried (MgSO4). Filtration and concentration gave the crude product which was chromatographed on RP HPLC to give the title compound which was isolated as the HCl salt.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto remove the DMF
  3. customthe residue partitioned between EtOAc and aq saturated NaHCO3 solution
  4. customthe organic layer separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and concentration
  8. customgave the crude product which
  9. customwas chromatographed on RP HPLC

Sources & evidence

ORD record
ord-62fcad5d5643416aab98ce465509f4ec
Source dataset
uspto-grants-2000_10
Patent number
US06127390

Reaction notes

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