Water → 5-Chloro-1-(5-chloro-2-(methylsulfonyl)benzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 1015702Notes

Reaction equation

HRID 1015702 reaction equation
[C:1]([CH:3]([CH:7]1[C:11]([Cl:12])=[C:10](Cl)C(=O)O1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([S:25]([CH3:28])(=[O:27])=[O:26])=[C:21]([CH2:23][NH2:24])[CH:22]=1.C(N(CC)C(C)C)(C)C.O>C(O)C>[ClH:12].[Cl:12][C:11]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1](=[NH:2])[N:24]([CH2:23][C:21]2[CH:22]=[C:17]([Cl:16])[CH:18]=[CH:19][C:20]=2[S:25]([CH3:28])(=[O:27])=[O:26])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 669698961-[5-Chloro-2-(methylsulfonyl)phenyl]methanamine hydrochloride

Product 1

HCID 669700865-Chloro-1-(5-chloro-2-(methylsulfonyl)benzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochlorideYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

(Step 4) To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.28 g) and 1-[5-chloro-2-(methylsulfonyl)phenyl]methanamine hydrochloride obtained in Step 3 (0.26 g) in ethanol (3 ml) was added N,N-diisopropylethylamine (0.44 ml) at room temperature, and the resulting mixture was heated under reflux for 4 hr. The reaction mixture was treated with water and stirred at 70° C. for 1 hr. After cooling to room temperature, the precipitate was collected by filtration and dried. The precipitate was suspended in methanol, and treated with a 2 M hydrogen chloride-methanol solution (0.3 ml). The resulting mixture was stirred at room temperature overnight. The precipitate was collected by filtration and dried to give the title compound (0.22 g) as white crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 hr
  3. temperatureAfter cooling to room temperature
  4. filtrationthe precipitate was collected by filtration
  5. customdried
  6. additiontreated with a 2 M hydrogen chloride-methanol solution (0.3 ml)
  7. stirringThe resulting mixture was stirred at room temperature overnight
  8. filtrationThe precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-e4fc92101b0f458eb0251e43726e39a4
Source dataset
uspto-grants-2011_07
Patent number
US07985862B2

Reaction notes

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