Pyridine → HCID 21075326, compound

HRID 1373708Notes

Reaction equation

HRID 1373708 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.[CH3:11][N:12]([CH:14]=O)[CH3:13].[N:16]1[CH:21]=CC=[CH:18][CH:17]=1.C(Cl)(=O)C([Cl:25])=O.[NH2:28][C:29]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:30]=1[C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][N:35]=1)=[O:32]>C(Cl)Cl>[ClH:25].[ClH:40].[Cl:45][C:42]1[CH:43]=[CH:44][C:29]([NH:28][C:8]([CH:5]2[CH2:4][CH2:3][CH:2]([N:16]3[CH2:17][CH2:18][CH2:13][N:12]([CH3:11])[CH2:14][CH2:21]3)[CH2:7][CH2:6]2)=[O:10])=[C:30]([CH:41]=1)[C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][N:35]=1)=[O:32]

Participants

7

Reactant 5

HCID 1049Pyridine2×HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1927304-Oxocyclohexanecarboxylic acidHCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 21075326HCID 21075326, compoundYield 492.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-oxocyclohexanoic acid (1 g, 7.03 mmol), CH2Cl2 (25 ml), DMF (0.016 mL, 0.211 mmol), and pyridine (0.58 ml, 7.25 mmol) at 0° C. was added oxalyl chloride (0.62 mL, 7.11 mmol); The reaction mixture was allowed to warm to room temperature and stirred for 1.5 h. This mixture was added to a 0° C. mixture of 2-amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide (2.0 g, 7.03 mmol), pyridine (0.85 mL, 10.6 mmol), and CH2Cl2 (25 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was filtered and the filtrate was concentrated and chromatographed (125 g silica gel, CH2Cl2 to 15% EtOAc/CH2Cl2) to give the title compound as a solid (600 mg, 21%).

Workup

  1. additionThis mixture was added to a 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customchromatographed (125 g silica gel, CH2Cl2 to 15% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-0b18048eec5b40d186a51fc63f185e69
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Reaction notes

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