Triethylamine → HCID 23154349, compound

HRID 492697Notes

Reaction equation

HRID 492697 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([Cl:16])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:17]([N:19]([CH2:22]C)[CH2:20][CH3:21])[CH3:18].ClC([O:27][C:28]1C=CC=CC=1)=O.C[N:35]1CCNCC1>O1CCCC1.CN(C)C=O>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:28]([N:35]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:17][CH2:18]3)=[O:27])[CH:7]=2)=[CH:10][C:11]=1[Cl:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 531671-MethylpiperazineHCID 229367984-(4-Amino-3-chlorophenoxy)pyridin-2-ylamine

Product 1

HCID 23154349HCID 23154349, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-(4-amino-3-chlorophenoxy)pyridine (236 mg) as disclosed in WO 02/32872 was dissolved in tetrahydrofuran (10 ml) under a nitrogen atmosphere, and then triethylamine (0.21 ml) and phenyl chloroformate (0.188 ml) were added dropwise thereto while cooling in an ice bath, followed by stirring at room temperature for 1.5 hrs. To the reaction mixture were added N,N-dimethylformamide (2 ml) and 1-methylpiperazine (0.555 ml), followed by further stirring for 1 day. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate:methanol=95:5) to provide the titled compound (234 mg, 65%) as pale brown powder.

Workup

  1. temperaturewhile cooling in an ice bath
  2. stirringby further stirring for 1 day
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (eluent; ethyl acetate:methanol=95:5)

Sources & evidence

ORD record
ord-cd9b7cc66cb344ebbc8eee34ad7c987d
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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