Triethylamine → HCID 22184843, compound

HRID 1795237Notes

Reaction equation

HRID 1795237 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:13](O)=O)[CH:4]=1.C([N:18]([CH2:21]C)CC)C.[OH:23]N1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[CH2:44]([O:46][C:47]([N:49]1[CH2:54][CH2:53][N:52]([C:55](CNCC(OCC)=O)=[O:56])[CH2:51][CH2:50]1)=[O:48])[CH3:45].[C:65]([O:68][CH2:69][CH3:70])(=[O:67])[CH3:66]>C(Cl)Cl>[CH2:44]([O:46][C:47]([N:49]1[CH2:50][CH2:51][N:52]([C:55]([CH2:13][C:5]2[C:4]([C:21]([NH:18][CH2:66][C:65]([O:68][CH2:69][CH3:70])=[O:67])=[O:23])=[C:3]([O:2][CH3:1])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=2)=[O:56])[CH2:53][CH2:54]1)=[O:48])[CH3:45]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5945964-Methoxy-2-quinolinecarboxylic acidHCID 22184797HCID 22184797, compound

Product 1

HCID 22184843HCID 22184843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-2-carboxyquinoline (102 mg, 0.50 mmol) in CH2Cl2 (15 mL) was added triethylamine (0.33 mL, 2.36 mmol) and 1-hydroxybenzotriazole (HOBT) (80 mg, 0.60 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) (110 mg, 0.60 mmol). After 5 minutes, 1-ethoxycarbonyl-4-(ethoxycarbonylmethyl)aminomethylcarbonylpiperazine (150 mg, 0.50 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was evaporated in vacuo to afford an oil, which was dissolved in ethyl acetate, and washed with saturated NaHCO3, 1M NaHSO4 and brine. The organic layer was evaporated in vacuo and the crude product was purified by flash column to afford 2-[(4-(ethoxycarbonyl)piperazin-1-yl)carbonylmethyl](ethoxycarbonylmethyl)aminocarbonyl-4-methoxyquinoline (30 mg).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto afford an oil, which
  3. washwashed with saturated NaHCO3, 1M NaHSO4 and brine
  4. customThe organic layer was evaporated in vacuo
  5. customthe crude product was purified by flash column

Sources & evidence

ORD record
ord-b3f530f23a4d4663b1993677ae623be7
Source dataset
uspto-grants-2006_04
Patent number
US07026323B2

Reaction notes

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