Dicyclohexylcarbodiimide → HCID 118023338, compound

HRID 929292Notes

Reaction equation

HRID 929292 reaction equation
[Cl:1][C:2]1[C:6]([NH:7][CH2:8][CH3:9])=[CH:5][N:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1.[CH3:16][N:17]([CH2:26][C:27]([OH:29])=O)[C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(OCC)C.C(Cl)Cl>[Cl:1][C:2]1[C:6]([N:7]([CH2:8][CH3:9])[C:27](=[O:29])[CH2:26][N:17]([CH3:16])[C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:5][N:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 75728Glycine, N-benzoyl-N-methyl-HCID 674989573-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine

Product 1

HCID 118023338HCID 118023338, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.075 g, 0.34 mmol), 2-(N-methylbenzamido)acetic acid (0.098 g, 0.51 mmol), and DMAP (0.062 g, 0.51 mmol) in dry diethyl ether (1.0 mL) and dry CH2Cl2 (1.1 mL) was cooled to a temperature of about 0° C. under N2. DCC (0.17 g, 0.81 mmol) was added, and the reaction was slowly warmed up to room temperature under N2, then stirred at room temperature overnight. The reaction mixture was filtered using additional CH2Cl2 (0.5 mL) to remove solids and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0%-10% MeOH/CH2Cl2 to afford the title compound F83 as a white solid (0.12 g, 87%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove solids
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 0%-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-5a52367868ab4985afeff7db88d51485
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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