1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22724077, compound

HRID 2086844Notes

Reaction equation

HRID 2086844 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:34])[NH:11][C:12]1[CH:13]=[C:14]([N:18]2[C:23](=[O:24])[C:22]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[N:21][C:20]3[CH:30]=[CH:31][CH:32]=[N:33][C:19]2=3)[CH:15]=[CH:16][CH:17]=1.O[N:36]1[C:40](=[O:41])[CH2:39][CH2:38][C:37]1=[O:42].C(N=C=NCCCN(C)C)C>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:34])[NH:11][C:12]1[CH:13]=[C:14]([N:18]2[C:23](=[O:24])[C:22]([CH2:25][CH2:26][C:27]([O:29][N:36]3[C:40](=[O:41])[CH2:39][CH2:38][C:37]3=[O:42])=[O:28])=[N:21][C:20]3[CH:30]=[CH:31][CH:32]=[N:33][C:19]2=3)[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 22724153HCID 22724153, compound

Product 1

HCID 22724077HCID 22724077, compoundYield 84.4%

Procedure

To a stirred solution of 4-[3-[3-(2-methoxyphenyl)ureido]phenyl]-3-oxo-2-(2-carboxyethyl)-3,4-dihydropyrido[2,3-b]pyrazine (2.30 g) and N-hydroxysuccinimide (1.15 g) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.20 g) and the resulting mixture was stirred for 24 hours. The reaction mixture was concentrated, diluted with ethyl acetate, washed with a saturated sodium bicarbonate solution, water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was triturated with ether to give 4-[3-[3-(2-methoxyphenyl)ureido]-phenyl]-3-oxo-2-[2-succinimidooxycarbonylethyl)-3,4-dihydropyrido[2,3-b]pyrazine (2.35 g) as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with a saturated sodium bicarbonate solution, water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-56cd8cd55c9949478db274086fa416b6
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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