Diisopropylethylamine → HCID 22057962, compound

HRID 1828717Notes

Reaction equation

HRID 1828717 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-amino-4-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-8570a530be634c11b3c62c4eb5098417
Source dataset
uspto-grants-2006_06
Patent number
US07060700B2

Reaction notes

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