Pyridine → HCID 15949952, compound

HRID 548757Notes

Reaction equation

HRID 548757 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C@H:8]([O:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][C:23]2[CH:35]=[CH:34][C:26]3[C:27](=[O:33])[N:28]([CH3:32])[CH2:29][CH2:30][O:31][C:25]=3[CH:24]=2)[CH:21]=1)[C:16]([OH:18])=O)[CH2:9][O:10][CH3:11].[NH2:36][C:37]1[CH:42]=[N:41][C:40]([CH3:43])=[CH:39][N:38]=1.N1C=CC=CC=1>CN(C=O)C.C(Cl)Cl>[CH3:7][C@H:8]([O:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][C:23]2[CH:35]=[CH:34][C:26]3[C:27](=[O:33])[N:28]([CH3:32])[CH2:29][CH2:30][O:31][C:25]=3[CH:24]=2)[CH:21]=1)[C:16]([NH:36][C:37]1[CH:42]=[N:41][C:40]([CH3:43])=[CH:39][N:38]=1)=[O:18])[CH2:9][O:10][CH3:11]

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 3132155-Methylpyrazin-2-amineHCID 57663207HCID 57663207, compound

Product 1

HCID 15949952HCID 15949952, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.17 mL, 1.94 mmol) and DMF (1 drop) were added to a solution of 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]benzoic acid (625 mg, 1.56 mmol) in DCM (15 mL) and the mixture stirred at RT for 4 hours. The solvent was evaporated in vacuo to a residue which was added to a solution of 2-amino-5-methylpyrazine (255 mg, 2.34 mmol) and pyridine (0.64 mL, 7.8 mmol) in DCM (5 mL). The resultant mixture was heated at 60° C. in a microwave reactor for 5 minutes. The mixture was cooled to RT and pressure, the DCM was evaporated in vacuo to a residue which was partitioned between ethyl acetate (50 mL) and 1N citric acid (25 mL). The organic layer was washed with 1N citric acid (25 mL), brine, dried (MgSO4) and evaporated in vacuo to a residue which was chromatographed on silica, eluting with ethyl acetate, to give the desired compound (352 mg).

Workup

  1. customThe solvent was evaporated in vacuo to a residue which
  2. temperatureThe mixture was cooled to RT
  3. custompressure, the DCM was evaporated in vacuo to a residue which
  4. customwas partitioned between ethyl acetate (50 mL) and 1N citric acid (25 mL)
  5. washThe organic layer was washed with 1N citric acid (25 mL), brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo to a residue which
  8. customwas chromatographed on silica
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-8b9af802fe0c43029e2dca68c3725b64
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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