1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664878, compound

HRID 1717316Notes

Reaction equation

HRID 1717316 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][F:22])=[C:15]([C:23]([OH:25])=O)[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1C=C[C:29]2N(O)N=[N:32][C:30]=2[CH:31]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[CH:30]1([NH:32][C:23]([C:15]2[N:14]=[N:13][N:12]([C:9]3[CH:8]=[CH:7][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=3)[C:16]=2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][F:22])=[O:25])[CH2:31][CH2:29]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68514380HCID 68514380, compound

Product 1

HCID 57664878HCID 57664878, compoundYield 212.1%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Ethylamino)carbonyl]phenyl}-5-(5-fluoropentyl)-1H-1,2,3-triazole-4-carboxylic acid (353 mg, 1.01 mmol) obtained in Example 111b), HOBt (55.3 mg, 0.405 mmol, 0.4 eq.) and cyclopropylamine (0.094 ml, 1.32 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 4.5 ml), WSC (218 mg, 1.11 mmol, 1.1 eq.) was added, and the mixture was stirred at room temperature for 12.5 hr. The reaction mixture was diluted with 2% aqueous sodium carbonate solution (20 ml), and the mixture was stirred at room temperature. The precipitate was collected by filtration, washed with water and dried to give a white powder. This was crystallized from ethyl acetate-diethyl ether, and the precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (333 mg, 0.859 mmol, 85.1%).

Workup

  1. stirringthe mixture was stirred at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried
  5. customto give a white powder
  6. customThis was crystallized from ethyl acetate-diethyl ether
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-2667520aea8c44bab28989353d002733
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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