1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66855664, compound

HRID 2282272Notes

Reaction equation

HRID 2282272 reaction equation
[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:17]4[S:18][C:19]([C:28](O)=[O:29])=[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:21]=4)=[C:14]([CH3:16])[N:15]=3)[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+].C1C=CC2N(O)N=[N:39]C=2C=1.CCN=C=NCCCN(C)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.O>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:17]4[S:18][C:19]([C:28]([NH2:39])=[O:29])=[C:20]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:21]=4)=[C:14]([CH3:16])[N:15]=3)[CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 66855231HCID 66855231, compound

Product 1

HCID 66855664HCID 66855664, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 2-(6-cyclohexyl-2-methylimidazo[1,2-a]pyridin-3-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid (169 mg, 0.405 mmol) obtained above in DMF (8 mL), were added TEA (170 μL, 1.22 mmol), ammonium chloride (65.0 mg, 1.22 mmol), HOBT (82 mg, 0.61 mmol) and EDCI (120 mg, 0.61 mmol), and the mixture was stirred at it for 12 h. To the mixture was added DMF (8.0 mL), and the mixture was stirred 40° C. for 2 h. The reaction mixture was allowed to cool to rt, DMF (30 mL) was added, and the mixture was warmed to 60° C. The solution was concentrated until ca 10 mL under reduced pressure. The residue was subjected to basic silica gel column chromatography (EtOAc/hexane=20/80→100/0; then MeOH/EtOAc=30/70). Concentration of the appropriate solution afforded crude product, which was suspended in saturated aqueous solution of sodium bicarbonate (10 mL) and water (10 mL). The resulting precipitate was collected by filtration and washed with water and diethyl ether to give the titled compound (104 mg, 62%) as a orange solid.

Workup

  1. stirringthe mixture was stirred 40° C. for 2 h
  2. temperaturethe mixture was warmed to 60° C
  3. concentrationThe solution was concentrated until ca 10 mL under reduced pressure
  4. customConcentration of the appropriate solution afforded crude product, which
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-0d4d83b26d1f4ff291187392f3700698
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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