1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68515662, compound

HRID 1717261Notes

Reaction equation

HRID 1717261 reaction equation
[CH2:1]([NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([CH2:20][CH2:21][CH3:22])=[C:18]([C:23]([OH:25])=O)[N:17]=[N:16]2)=[CH:11][CH:10]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].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>[CH:30]1([NH:32][C:23]([C:18]2[N:17]=[N:16][N:15]([C:12]3[CH:11]=[CH:10][C:9]([C:7]([NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[O:8])=[CH:14][CH:13]=3)[C:19]=2[CH2:20][CH2:21][CH3:22])=[O:25])[CH2:31][CH2:29]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68515310HCID 68515310, compound

Product 1

HCID 68515662HCID 68515662, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Pentylamino)carbonyl]phenyl}-5-propyl-1H-1,2,3-triazole-4-carboxylic acid (487 mg, 1.41 mmol) obtained in Example 57b), HOBt (193 mg, 1.41 mmol, 1.0 eq.) and cyclopropylamine (0.131 ml, 1.84 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (1:1, 7.5 ml), WSC (332 mg, 1.70 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, dissolved in ethyl acetate (40 ml), and washed with 5% aqueous sodium hydrogen carbonate solution, 10% aqueous ammonium chloride solution and saturated brine. The aqueous layers were each extracted with ethyl acetate-hexane (2:1, 30 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to give a white powder. This was crystallized from methanol-ethyl acetate to give the title compound as a white powder (298 mg, 0.777 mmol, 55.1%). The mother liquor was concentrated, and crystallized from diethyl ether to give the title compound as a white powder (225 mg, 0.587 mmol, 41.6%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (40 ml)
  3. washwashed with 5% aqueous sodium hydrogen carbonate solution, 10% aqueous ammonium chloride solution and saturated brine
  4. extractioneach extracted with ethyl acetate-hexane (2:1, 30 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto give a white powder
  8. customThis was crystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-79d070e6f93a44eeb760bb7e01491dac
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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