Diisopropylethylamine → HCID 22057962, compound

HRID 2302242Notes

Reaction equation

HRID 2302242 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:33])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:30]([CH3:32])[CH3:31])[CH:25]=2)[CH:18]=[CH:19][C:20]=1[CH3:21].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:32][N:30]([CH3:31])[C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[C:23]([NH:22][C:17]1[CH:18]=[CH:19][C:20]([CH3:21])=[C:15]([NH:14][C:11]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:13])[CH:16]=1)=[O:33]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 825716-Quinolinecarboxylic acidHCID 22057981HCID 22057981, compound

Product 1

HCID 22057962HCID 22057962, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Quinolinecarboxylic acid (0.173 g) was added to a stirred suspension of N-(3-amino4-methylphenyl)3-dimethylaminobenzamide (0.135 g), diisopropylethylamine (0.325 ml), 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.39 g) in DMF (10 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The solvent was evaporated and the residue was dissolved in methylene chloride and washed with a saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated. The residue was triturated under a mixture of ethyl acetate and isohexane. There was thus obtained the title compound as a solid (0.052 g); NMR Spectrum: (DMSOd6) 2.24 (s, 3H), 2.95 (s, 6H), 6.89 (d, 1H), 7.25 (m, 4H), 7.6 (m, 2H), 7.85 (s, 1H), 8.12 (d, 1H), 8.4 (d, 1H), 8.52 (d, 1H), 8.65 (m, 1H), 8.99 (d, 1H), 10.11 (s, 1H), 10.16 (s, 1H); Mass Spectrum: M+H+ 425.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed with a saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was triturated under a mixture of ethyl acetate and isohexane

Sources & evidence

ORD record
ord-24b4cba271664471a651b102cdc50b24
Source dataset
uspto-grants-2002_08
Patent number
US06432949B1

Reaction notes

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