Pyridine → HCID 53629666, compound

HRID 1990221Notes

Reaction equation

HRID 1990221 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][CH:8]([O:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=1)[C:14]([OH:16])=O)[CH3:9].[NH2:28][C:29]1[CH:34]=[N:33][C:32]([CH3:35])=[CH:31][N:30]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:9][CH:8]([O:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=1)[C:14]([NH:28][C:29]1[CH:34]=[N:33][C:32]([CH3:35])=[CH:31][N:30]=1)=[O:16])[CH3:7]

Participants

6

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 3132155-Methylpyrazin-2-amineHCID 534011033-Benzyloxy-5-isopropoxybenzoic acid

Product 1

HCID 53629666HCID 53629666, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (2.1 mL, 24.0 mmol) was added to a solution of 3-[(1-methylethyl)oxy]-5-[(phenylmethyl)oxy]benzoic acid (5.72 g, 20.0 mmol) in DCM (100 mL) and the mixture stirred at ambient RT for 4 hours. The mixture was evaporated in vacuo to a residue, which was taken up in DCM (25 mL) and added to a stirred mixture of 2-amino-5-methylpyrazine (2.29 g, 21.0 mmol) and pyridine (1.94 mL, 24.0 mmol) in DCM (100 mL) at 5° C.-10° C. The mixture was stirred at RT for 18 hours, the DCM evaporated in vacuo to a residue, which was partitioned between water (50 mL) and ethyl acetate (150 mL). The organic layer was washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with 30% ethyl acetate in isohexane, and crystallised from ethyl acetate/isohexane to give the desired compound (5.52 g).

Workup

  1. customThe mixture was evaporated in vacuo to a residue, which
  2. stirringThe mixture was stirred at RT for 18 hours
  3. customthe DCM evaporated in vacuo to a residue, which
  4. customwas partitioned between water (50 mL) and ethyl acetate (150 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to a residue which
  8. customwas chromatographed on silica
  9. washeluting with 30% ethyl acetate in isohexane
  10. customcrystallised from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-c7b4f7e33e1b4bb9a5a2bbb09b274ab9
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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