2-Chloropyridine → HCID 12973106, compound

HRID 411299Notes

Reaction equation

HRID 411299 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([N:15]([CH2:17][C:18]1([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:16])[N:7]=[C:6]2[NH2:30].Cl[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1>CN1CCCC1=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([N:15]([CH3:16])[CH2:17][C:18]1([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:20][N:21]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[CH2:22][CH2:23]1)[N:7]=[C:6]2[NH2:30]

Participants

5

Reactant 2

HCID 79772-ChloropyridineHCID 11486612HCID 11486612, compound

Product 1

HCID 12973106HCID 12973106, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 6,7-dimethoxy-N2-(4-phenyl-piperidin-4-ylmethyl)-N2-methyl-quinazoline-2,4-diamine 11 (250 mg) and 2-chloropyridine in N-methylpyrrolidone (5 m) was stirred at 130° C. under nitrogen for 48 hours. The cooled reaction mixture was diluted with water and extracted with chloroform. The extract was chromatographed on silica gel to yield 6,7-dimethoxy-N2-methyl-N2-(4-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylmethyl)-quinazoline-2,4-diamine 22, MS: 485 ([M+H]+).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with chloroform
  3. customThe extract was chromatographed on silica gel

Sources & evidence

ORD record
ord-6177dfb8e4ef43838b9023a15327569f
Source dataset
uspto-grants-2003_05
Patent number
US06559153B2

Reaction notes

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