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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57665017, compound

HRID 1717304
Notes
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Reaction equation

HRID 1717304 reaction equation
[CH:1]1([CH2:7][C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=3)[N:11]=[N:10][C:9]=2[C:24]([OH:26])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C[C:30]2N(O)N=[N:33][C:31]=2[CH:32]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.C(=O)([O-])O.[Na+].O>[CH:1]1([CH2:7][C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:18]=3)[N:11]=[N:10][C:9]=2[C:24]([NH:33][CH:31]2[CH2:32][CH2:30]2)=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68513203HCID 68513203, compound

Product 1

HCID 57665017HCID 57665017, compoundYield 183.6%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 516892Sodium BicarbonateSolvent
HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

5-(Cyclohexylmethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid (357 mg, 1.00 mmol) obtained in Example 102b), HOBt (68.2 mg, 0.500 mmol, 0.5 eq.) and cyclopropylamine (0.093 ml, 1.30 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 4.5 ml), WSC (215 mg, 1.10 mmol, 1.1 eq.) was added, and the mixture was stirred at room temperature for 14 hr. Water was added to the reaction mixture, and the obtained suspension was diluted with 2% aqueous sodium hydrogen carbonate solution. The precipitate was collected by filtration, washed with water and dried to give the title compound as a white powder (363 mg, 0.918 mmol, 91.8%).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-df5c375ef883454ebe22f0ea1228dee6
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07803822B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes