6-Quinolinecarboxylic acid → HCID 9867182, compound

HRID 1828720Notes

Reaction equation

HRID 1828720 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:14][C:15]1[CH:16]=[C:17]([NH:22][C:23](=[O:32])[C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]>>[Cl:21][C:20]1[CH:19]=[CH:18][C:17]([NH:22][C:23](=[O:32])[C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)=[CH:16][C:15]=1[NH:14][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)=[O:13]

Participants

3

Reactant 2

HCID 825716-Quinolinecarboxylic acidHCID 16793499HCID 16793499, compound

Product 1

HCID 9867182HCID 9867182, compoundYield 18%

Procedure

Using an analogous procedure to that described in Example 3, quinoline-6-carboxylic acid was reacted with N-(3-amino-4-chlorophenyl)-4-cyanobenzamide. The crude reaction product was purified by column chromatography on silica using a 97:3 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound in 18% yield; NMR Spectrum: (DMSOd6) 7.58 (d, 1H), 7.62 (m, 1H), 7.77 (m, 1H), 8.01 (d, 2H), 8.12 (t, 4H), 8.28 (d, 2H), 8.56 (d, 1H), 8.67 (s, 1H), 9.01 (d, 1H), 10.34 (s, 1H), 10.67 (s, 1H); Mass Spectrum: M−H− 425.

Workup

  1. customThe crude reaction product
  2. customwas purified by column chromatography on silica using
  3. additiona 97:3 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-c8a8bde7d4d34423b3e8e8316b6e415b
Source dataset
uspto-grants-2006_06
Patent number
US07060700B2

Reaction notes

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