Pyridine → HCID 90403384, compound

HRID 1049357Notes

Reaction equation

HRID 1049357 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]1.C(Cl)(=O)[C:11](Cl)=[O:12].[Cl:16][C:17]1[CH:22]=[C:21]([O:23][C:24]2[CH:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)[CH:20]=[CH:19][N:18]=1.N1C=CC=CC=1>ClCCCl.C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[C:21]([O:23][C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:11]([NH:9][C:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[O:8])=[O:12])=[N:28][CH:29]=2)[CH:20]=[CH:19][N:18]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 13197203Oxane-4-carboxamideHCID 593227885-(2-Chloropyridin-4-yloxy)pyridin-2-amine

Product 1

HCID 90403384HCID 90403384, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of Example B5 (0.568 g, 4.40 mmol) and oxalyl chloride (0.400 mL, 4.66 mmol) in DCE (10 mL) was heated at 100° C. for 1 h, cooled to RT, added to a solution of Example A9 (0.650 g, 2.93 mmol) and pyridine (0.400 mL, 4.96 mmol) in DCM (10 mL) and stirred at RT for 2 days. The mixture was treated with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN, sonicated, the solid collected via filtration and purified via silica gel chromatography (MeOH/DCM) to afford N-((5-((2-chloropyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydro-2H-pyran-4-carboxamide (335 mg, 30%) as a white solid. MS (ESI) m/z: 377.1 (M+H+).

Workup

  1. additionThe mixture was treated with satd
  2. extractionNaHCO3, extracted with EtOAc (3×)
  3. dry with materialthe combined organics were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. additionThe material was treated with MeCN
  6. customsonicated
  7. filtrationthe solid collected via filtration
  8. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-67bf041b36f14347895f868c1f958e0b
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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