1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10711401, compound

HRID 977185Notes

Reaction equation

HRID 977185 reaction equation
[C:1]([CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:16])=[CH:13][CH:14]=2)[NH:9][C:8](=[O:17])[C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(O)=[O:2].C([O-])(=O)C.[NH4+].O[N:30]1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>O1CCCC1.O.C(N(CC)CC)C>[NH2:30][C:1]([CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:16])=[CH:13][CH:14]=2)[NH:9][C:8](=[O:17])[C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:2]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 517165Ammonium AcetateHCID 10544360HCID 10544360, compound

Product 1

HCID 10711401HCID 10711401, compoundYield 31.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-carboxymethoxy-7-chloro-3-phenyl--2(1H)-quinolone (0.93 g Example 15) in tetrahydrofuran (50 ml) under nitrogen at room temperature, was added triethylamine (1.90 ml), ammonium acetate (0.50 g), 1-hydroxybenzotriazole (0.60 g) and 1-(3 dimethylaminopropyl)-3-ethyl carbodiimide (0.90 g). The reaction mixture was stirred at room temperature for 3 days, then poured into water (100 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with 1N citric acid (1×75 ml), water (1×75 ml), saturated sodium hydrogen carbonate (1×75 ml) and brine (1×75 ml), then dried (MgSO4), filtered and the solvent was removed in vacuo to leave a solid residue. Recrystallisation from MeOH gave the title compound (0.29 g). Mp 262°-264° C. Found: C, 66.31; H, 5.95; N, 7.46; C19H19N2O2Cl 0.1C6H14 0.6H2O requires C, 65.97; H, 5.93; N, 7.85%. δ (360 MHz, DMSO-d6) 3.91 (2H, s, OCH2CONH2), 7.25-7.45 (9H, m, Ph+6H+8-H+OCH2CONH2), 8.01 (1H, d, J=8.66 Hz, 5-H), 11.92 (1H, bs, NH). m/z (CI+), 329, (M+1).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined organic layers were washed with 1N citric acid (1×75 ml), water (1×75 ml), saturated sodium hydrogen carbonate (1×75 ml) and brine (1×75 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customto leave a solid residue
  7. customRecrystallisation from MeOH

Sources & evidence

ORD record
ord-70327acf8b0f43718dd48fef330b80b5
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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