Triethylamine → HCID 23153150, compound

HRID 492699Notes

Reaction equation

HRID 492699 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=2)=[CH:4][C:3]=1[Cl:16].C(N(CC)CC)C.Cl[C:25](OC1C=CC=CC=1)=[O:26].[N:34]1([CH2:40][CH2:41][CH2:42][NH2:43])[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:25]([NH:43][CH2:42][CH2:41][CH2:40][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[O:26])[CH:8]=2)=[CH:4][C:3]=1[Cl:16]

Participants

8

Reactant 4

HCID 8471Triethylamine3×HCID 15891Phenyl chloroformate3×HCID 61055N-(3-Aminopropyl)morpholineHCID 229367984-(4-Amino-3-chlorophenoxy)pyridin-2-ylamine

Product 1

HCID 23153150HCID 23153150, compoundYield 27.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Amino-3-chlorophenoxy)pyridin-2-ylamine (750 mg, 3.18 mmol) was dissolved in tetrahydrofuran (30 ml), and then triethylamine (0.444 ml, 4.77 mmol) was added thereto. Phenyl chloroformate (0.399 ml, 4.77 mmol) was added dropwise thereto while ice-cooling, followed by stirring at room temperature for 4 hrs and 45 min. Triethylamine (0.222 ml) and phenyl chloroformate (0.200 ml) were further added thereto while ice-cooling, followed by stirring for 40 min. Triethylamine (0.111 ml) and phenyl chloroformate (0.100 ml) were further added thereto, followed by stirring for 40 min. The reaction mixture was concentrated under a reduced pressure to give a residue, to which N,N-dimethylformamide (10 ml) and 3-(morpholin-4-yl)propylamine (2.32 ml, 15.9 mmol) were added, followed by stirring at room temperature for 2 hrs. The reaction mixture was partitioned between ethyl acetate (50 ml) and water (20 ml). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a solid, which was then suspended in ethyl acetate, filtered, washed with ethyl acetate, and dried under aeration to provide the titled compound (359 mg, 0.844 mmol, 27.8%) as colorless powder.

Workup

  1. temperaturewhile ice-cooling
  2. temperaturewhile ice-cooling
  3. stirringby stirring for 40 min
  4. stirringby stirring for 40 min
  5. concentrationThe reaction mixture was concentrated under a reduced pressure
  6. customto give a residue
  7. stirringby stirring at room temperature for 2 hrs
  8. customThe reaction mixture was partitioned between ethyl acetate (50 ml) and water (20 ml)
  9. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated
  12. customto give a solid, which
  13. filtrationfiltered
  14. washwashed with ethyl acetate
  15. customdried under aeration

Sources & evidence

ORD record
ord-909141310f464bc885e189f0cdb1613f
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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