Dicyclohexylcarbodiimide → HCID 10762413, compound

HRID 651055Notes

Reaction equation

HRID 651055 reaction equation
[NH2:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([OH:14])=O)=[CH:9][CH:8]=[CH:7][CH:6]=2.ON1C2C=CC=CC=2N=N1.[CH2:31]([C@H:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1.CC#N.C(Cl)Cl>[CH2:31]([C@H:33]([NH:40][C:12]([C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:2]=1[NH2:1])=[O:14])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 6993773(1S)-1-phenylpropan-1-amineHCID 10515736HCID 10515736, compound

Product 1

HCID 10762413HCID 10762413, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 22177404Acetonitrile tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.5 g (5.7 mmol) of 3-amino-2-phenylquinoline-4-carboxylic acid (CAS [36735-26-9]) were dissolved in 140 ml of a 7/3 mixture of THF/CH3CN; 1.5 g (11.1 mmol) of 1-hydroxybenzotriazole (HOBT) were added and 1.15 g (8.5 mmol) of (S)-α-ethyl benzylamine dissolved in 10 ml of CH2Cl2 were added dropwise. After cooling of the reaction mixture to 0° C., 1.4 g (6.7 mmol) of dicyclohexylcarbodiimmide (DCC) dissolved in 10 ml of CH2Cl2 were added dropwise. The solution was kept at 0° C. for 30 minutes and then at room temperature overnight. The reaction mixture was evaporated in-vacuo, the residue was dissolved in CH2Cl2 and the solution filtered off, washed with H2O, 20% citric acid, sat. sol. NaHCO3 and sat. sol. NaCl. The organic layer was separated, drive over Na2SO4 and evaporated in-vacuo to dryness to obtain 2.4 g of the crude product. This was triturated with i-Pr2O, then recrystallized with a 10:1 mixture of iPr2O/i-PrOH to yield 1.7 g of the title compound.

Workup

  1. additionwere added dropwise
  2. additionwere added dropwise
  3. customat room temperature
  4. customovernight
  5. customThe reaction mixture was evaporated in-vacuo
  6. dissolutionthe residue was dissolved in CH2Cl2
  7. filtrationthe solution filtered off
  8. washwashed with H2O, 20% citric acid, sat. sol. NaHCO3 and sat. sol. NaCl
  9. customThe organic layer was separated
  10. customdrive over Na2SO4 and evaporated in-vacuo to dryness
  11. customto obtain 2.4 g of the crude product
  12. customThis was triturated with i-Pr2O
  13. customrecrystallized with a 10:1 mixture of iPr2O/i-PrOH

Sources & evidence

ORD record
ord-f2d22b26e63548ad802c952f2ac92470
Source dataset
uspto-grants-2001_08
Patent number
US06277862B1

Reaction notes

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