1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 16222145, compound

HRID 1717314Notes

Reaction equation

HRID 1717314 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][F:21])=[C:15]([C:22]([OH:24])=O)[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1C=C[C:28]2N(O)N=[N:31][C:29]=2[CH:30]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.C(=O)([O-])[O-].[Na+].[Na+].O>[CH:29]1([NH:31][C:22]([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][F:21])=[O:24])[CH2:30][CH2:28]1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68514256HCID 68514256, compound

Product 1

HCID 16222145HCID 16222145, compoundYield 176.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 10340Sodium CarbonateSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Ethylamino)carbonyl]phenyl}-5-(4-fluorobutyl)-1H-1,2,3-triazole-4-carboxylic acid (375 mg, 1.12 mmol) obtained in Example 108b), HOBt (76.5 mg, 0.561 mmol, 0.5 eq.) and cyclopropylamine (0.104 ml, 1.46 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 4.5 ml), WSC (263 mg, 1.35 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with 2% aqueous sodium carbonate solution (5 ml) and water (10 ml), and the mixture was stirred at room temperature. The precipitate was collected by filtration, washed with water and dried to give the title compound as a white powder (369 mg, 0.988 mmol, 88.2%).

Workup

  1. stirringthe mixture was stirred at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ddf80ff51f524a41be600f7866a8f438
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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