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

HRID 853271Notes

Reaction equation

HRID 853271 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-3f2bc1c5bf9e49c4941e55e57234f484
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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