1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 19965408, compound

HRID 977186Notes

Reaction equation

HRID 977186 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)([OH:3])=O.Cl.[CH3:25][O:26][NH2:27].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>O1CCCC1.O.C(N(CC)CC)C>[Cl:16][C:12]1[CH:11]=[C:10]2[C:15]([C:6]([O:5][CH2:4][C:1]([NH:27][O:26][CH3:25])=[O:3])=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8](=[O:17])[NH:9]2)=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 521874O-Methylhydroxylamine hydrochlorideHCID 10544360HCID 10544360, compound

Product 1

HCID 19965408HCID 19965408, compoundYield 6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-carboxymethoxy-7-chloro-3-phenyl-2(1H)-quinolone (Example 15, 1.83 g) in tetrahydrofuran (150 ml) under nitrogen at room temperature, was added triethylamine (3.65 ml), O-methyl hydroxylamine hydrochloride (0.96 g), 1-hydroxybenzotriazole (1.15 g) and 1-(3 dimethylaminopropyl)-3-ethyl carbodiimide (1.73 g). The reaction mixture was stirred at room temperature for 16 h, then poured into water (150 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water (1×100 ml), 1N citric acid (1×100 ml), brine (1×100 ml) and a saturated sodium hydrogen carbonate solution (1×50 ml), dried (MgSO4), filtered and the solvent was removed in vacuo to leave a solid residue. Recrystallisation from ethyl acetate gave the title compound (0.12 g). Mp 205°-207° C. m/z (CI+), 359, (m+1). 1H NMR (360 MHz, DMSO-d6) δ 3.32 (3H, s, NHOCH3), 3.93 (2H, s, OCH2CONHOCH3), 7.23 (1H, dd, J=8.63 Hz, J=1.83 Hz, 6-H), 7.36-7.45 (6H, m, Ph+8-H), 8.00 (1H, d, J=8.63 Hz, 5-H), 11.26 (1H, bs, OCH2CONHOCH3), 11.94 (1H, bs, NH). Found: C, 60.57; H, 4.26; N, 7.82; C18H15N2O4Cl requires C, 60.26; H, 4.21; N, 7.81%.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined organic layers were washed with water (1×100 ml), 1N citric acid (1×100 ml), brine (1×100 ml)
  3. dry with materiala saturated sodium hydrogen carbonate solution (1×50 ml), dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customto leave a solid residue
  7. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-7e3912e22ffe4dd1a01599d12277abe8
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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