Dimethylformamide → HCID 86677638, compound

HRID 1499693Notes

Reaction equation

HRID 1499693 reaction equation
N1C(Cl)=NC(Cl)=NC=1[Cl:3].CN(C)C=O.[Cl:15][C:16]1[C:17]([CH3:39])=[C:18]([C:28]2[CH:29]=[CH:30][C:31]([C:34]([N:36]([CH3:38])[CH3:37])=[O:35])=[N:32][CH:33]=2)[C:19]([O:25][CH2:26][CH3:27])=[C:20]([CH:22](O)[CH3:23])[CH:21]=1>ClCCl>[Cl:15][C:16]1[C:17]([CH3:39])=[C:18]([C:28]2[CH:29]=[CH:30][C:31]([C:34]([N:36]([CH3:38])[CH3:37])=[O:35])=[N:32][CH:33]=2)[C:19]([O:25][CH2:26][CH3:27])=[C:20]([CH:22]([Cl:3])[CH3:23])[CH:21]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 86677639HCID 86677639, compound

Product 1

HCID 86677638HCID 86677638, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyanuric chloride (0.43 g, 2.3 mmol) was added to N,N-dimethylformamide (0.18 mL, 2.3 mmol) at room temperature. After the formation of a white solid (10 minutes), methylene chloride (10 mL) was added, followed by 5-[3-chloro-6-ethoxy-5-(1-hydroxyethyl)-2-methylphenyl]-N,N-dimethylpyridine-2-carboxamide (0.6 g, 2 mmol). After addition, the mixture was stirred at room temperature overnight, then diluted with dichloromethane and washed with sat. NaHCO3 solution. The organic layers were dried over MgSO4, concentrated. The residue was purified on silica gel (eluting with 0 to 50% EtOAc in hexanes) to give the desired product (0.58, 90%). LCMS calculated for C19H23Cl2NO2 (M+H)+: m/z=381.1; Found: 381.0.

Workup

  1. additionAfter addition
  2. washwashed with sat. NaHCO3 solution
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (eluting with 0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c89be02615924ff5a62ec0860f301ced
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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