1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68518414, compound

HRID 1717271Notes

Reaction equation

HRID 1717271 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[C:22]([CH2:23][CH2:24][CH3:25])=[C:21]([C:26]([O-])=[O:27])[N:20]=[N:19]3)=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na+].C1C=C[C:33]2N(O)N=[N:36][C:34]=2[CH:35]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C>[CH:34]1([NH:36][C:26]([C:21]2[N:20]=[N:19][N:18]([C:15]3[CH:16]=[CH:17][C:12]([C:10]([NH:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:11])=[CH:13][CH:14]=3)[C:22]=2[CH2:23][CH2:24][CH3:25])=[O:27])[CH2:35][CH2:33]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68512653HCID 68512653, compound

Product 1

HCID 68518414HCID 68518414, compoundYield 138.9%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

Sodium 1-(4-{[(2-morpholin-4-ylethyl)amino]carbonyl}phenyl)-5-propyl-1H-1,2,3-triazole-4-carboxylate (642 mg, 1.34 mmol) obtained in Example 61b), HOBt (91.6 mg, 0.671 mmol, 0.5 eq.) and cyclopropylamine (0.125 ml, 1.74 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 9.0 ml), WSC (315 mg, 1.61 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated, dissolved in ethyl acetate (35 ml) and washed with 2% aqueous sodium carbonate solution and saturated brine. The aqueous layers were each extracted with ethyl acetate (25 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated, and ethyl acetate and diethyl ether were added. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (397 mg, 0.932 mmol, 69.6%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (35 ml)
  3. washwashed with 2% aqueous sodium carbonate solution and saturated brine
  4. extractioneach extracted with ethyl acetate (25 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. additionethyl acetate and diethyl ether were added
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-983624ee939246fb89c4e26eb754496e
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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