4-Quinolinecarboxylic acid → HCID 178461347, compound

HRID 2302054Notes

Reaction equation

HRID 2302054 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](C(O)=O)=[CH:3][CH:2]=1.[C:14]([N:21]1[CH:25]=[CH:24]N=C1)(N1C=CN=C1)=[O:15].Cl.[CH3:27][C@H:28]1[CH2:33]C[C@H](N)[CH2:30][CH2:29]1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:27][C@H:28]1[CH2:33][CH2:24][C@H:25]([NH:21][C:14]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:15])[CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 102434-Quinolinecarboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 178461307HCID 178461307, compound

Product 1

HCID 178461347HCID 178461347, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of quinoline-4-carboxylic acid (173 mg, 1 mmol), and 1,1′-carbonyldiimidazole (162 mg, 1 mmol) in dimethylformamide (2 mL) was heated at 50° C. for 1 hour. After this time, trans-4-methylcyclohexylamine hydrochloride (150 mg, 1 mmol), and N,N-diisopropylethylamine (0.262 mL, 1.5 mmol) were added and the mixture heated at 50° C. for 16 hours. The reaction mixture was cooled, and diluted with chloroform (10 mL). The organic solution was washed with water (3×10 mL), 1 N NaOH (10 mL), brine (10 mL), dried over anhydrous MgSO4, filtered and concentrated to afford 224 mg (84%) of 404:

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe organic solution was washed with water (3×10 mL), 1 N NaOH (10 mL), brine (10 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fde540677bfe4b6189833ce9c76846ac
Source dataset
uspto-grants-2002_08
Patent number
US06429207B1

Reaction notes

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