1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22937025, compound

HRID 1010134Notes

Reaction equation

HRID 1010134 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])[N:9]=[CH:8][CH:7]=[C:6]2[O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[O:29])=[C:23]([F:38])[CH:22]=1)#[N:2].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH:60]1([NH2:63])[CH2:62][CH2:61]1.O.[OH-].[Na+]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][C:17]([NH:63][CH:60]1[CH2:62][CH2:61]1)=[O:18])[N:9]=[CH:8][CH:7]=[C:6]2[O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)=[O:29])=[C:23]([F:38])[CH:22]=1)#[N:2]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 22936808HCID 22936808, compoundHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 22937025HCID 22937025, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-(6-Cyano-7-(3-carboxypropoxy)-4-quinolyl)oxy-2-fluorophenyl)-N′-(4-fluorophenyl)urea (100 mg) was dissolved in dimethylformamide (3 ml), and then 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (44 mg) and 1-hydroxy-1H-benzotriazole (35 mg) were added while stirring on ice and the mixture was stirred at room temperature for 30 minutes. Cyclopropylamine (16 μl) was then added and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction solution was poured into 1N sodium hydroxide water and extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine and dried over magnesium sulfate. The organic layer was concentrated, and the obtained solid was washed with ether and a small amount of ethyl acetate to obtain 38 mg of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washthe obtained organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe organic layer was concentrated
  8. washthe obtained solid was washed with ether

Sources & evidence

ORD record
ord-3375607ebf2a464e9099d3fb44805707
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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