Sodium Carbonate → HCID 68514328, compound

HRID 1717265Notes

Reaction equation

HRID 1717265 reaction equation
[C: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])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C[C:32]2N(O)N=[N:35][C:33]=2[CH:34]=1.C1(N)CC1.CCN=C=NCCCN(C)C.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CN(C=O)C>[CH:33]1([NH:35][C:26]([C:21]2[N:20]=[N:19][N:18]([C:15]3[CH:14]=[CH:13][C:12]([C:10]([NH:9][CH2:8][CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[O:11])=[CH:17][CH:16]=3)[C:22]=2[CH2:23][CH2:24][CH3:25])=[O:27])[CH2:34][CH2:32]1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68515063HCID 68515063, compound

Product 1

HCID 68514328HCID 68514328, compoundYield 149.9%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-(4-{[(2-Phenylethyl)amino]carbonyl}phenyl)-5-propyl-1H-1,2,3-triazole-4-carboxylic acid (510 mg, 1.35 mmol) obtained in Example 59b), HOBt (92 mg, 0.674 mmol, 0.5 eq.) and cyclopropylamine (0.125 ml, 1.75 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 9.0 ml), WSC (316 mg, 1.62 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2 hr. 2% Aqueous sodium carbonate solution (10 ml) was added to the reaction mixture and the mixture was stirred at room temperature for 1 hr. The precipitate was collected by filtration, washed with ice-cold water and dried to give a grayish white powder. This was crystallized from methanol-diethyl ether to give the title compound as a white powder (421 mg, 1.01 mmol, 74.7%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ice-cold water
  4. customdried
  5. customto give a grayish white powder
  6. customThis was crystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-68088d0d27b84f309c45b2bebe6e60fb
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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