2-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide → HCID 16731823, compound

HRID 2300946Notes

Reaction equation

HRID 2300946 reaction equation
Cl.[C:2]([C:5]1[S:6][CH:7]=[C:8]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[C:9]=1[Cl:10])([OH:4])=O.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:36])[C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[NH2:35])=[N:24][CH:25]=1>S(Cl)(Cl)=O.N1C=CC=CC=1>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:36])[C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[NH:35][C:2]([C:5]2[S:6][CH:7]=[C:8]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[C:9]=2[Cl:10])=[O:4])=[N:24][CH:25]=1

Participants

5

Reactant 2

HCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamideHCID 69832497HCID 69832497, compound

Product 1

HCID 16731823HCID 16731823, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 2-carboxy-3-chloro-4-(4-methylpiperazin-1-yl)methylthiophene HCl salt (2.0 g, 5.8 mmol) in thionyl chloride (50 mL) was heated at reflux. After 90 hours, the mixture was cooled to ambient temperature and concentrated of all volatiles in vacuo. To a suspension of the resulting solid in pyridine (20 mL) at 0° C. was added N-(5-chloropyridin-2-yl)-2-amino-5-chlorobenzamide (1.5 g, 5.2 mmol) in pyridine (5 mL). The mixture was stirred and allowed to warm gradually to ambient temperature. After 16 hours, the mixture was concentrated of all volatiles in vacuo. Purification by flash chromatography on silica gel afforded 2.2 g (80% yield) of N-(5-chloropyridin-2-yl)-2-[((4-((4-methylpiperazin-1-yl)methyl)-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide, as a tan foam; NMR (DMSO-d6/TFA) 11.4 (s, 1), 11.0 (s, 1), 7.6-8.4 (m, 7), 4.4 (s, 2), 3.0-4.0 (br m, 8), 2.9 (s, 3) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. concentrationconcentrated of all volatiles in vacuo
  4. additionTo a suspension of the resulting solid in pyridine (20 mL) at 0° C.
  5. temperatureto warm gradually to ambient temperature
  6. waitAfter 16 hours
  7. concentrationthe mixture was concentrated of all volatiles in vacuo
  8. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-af6e3c72cabe42d4bd077795d8f0194f
Source dataset
uspto-grants-2002_12
Patent number
US06498185B1

Reaction notes

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