Triethylamine → HCID 58886645, compound

HRID 494706Notes

Reaction equation

HRID 494706 reaction equation
[CH2:1]([N:3](CC)CC)C.[C:8]([O:12][C:13](=[O:31])[C:14]1[C:19]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=2[Cl:28])=[C:18]([Cl:29])[C:17](Cl)=[N:16][CH:15]=1)([CH3:11])([CH3:10])[CH3:9].CCO[C:35]([CH3:37])=[O:36]>C(#N)C>[C:8]([O:12][C:13](=[O:31])[C:14]1[C:19]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=2[Cl:28])=[C:18]([Cl:29])[C:17]([NH:3][CH2:1][CH:35]([OH:36])[CH3:37])=[N:16][CH:15]=1)([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 58886663HCID 58886663, compound

Product 1

HCID 58886645HCID 58886645, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

I-Amino-propan-2-ol (2.44 g, 30.3 mmol) and triethylamine (0.42 mL, 3.03 mmol) were added to a solution of 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid tert-butyl ester (1.37 g, 3.03 mmol) in acetonitrile (30 mL). The reaction was heated to reflux. After 23 hours the reaction was cooled to room temperature and diluted with EtOAc, washed with saturated NaHCO3, water, brine, dried over Na2SO4 and concentrated to a white solid. Purification by flash column chromatography (20:1 dichloromethane/methanol) provided the desired product as a white solid (1.11 g, 75%). MS APCI (+) m/z 492, 494 (M+, Cl, Br pattern) detected.

Workup

  1. temperatureThe reaction was heated to reflux
  2. washwashed with saturated NaHCO3, water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a white solid
  5. customPurification by flash column chromatography (20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-4efdbf5bba36459d973625b1a8d892df
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

Loading…