Pyridine → HCID 59186704, compound

HRID 731537Notes

Reaction equation

HRID 731537 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][C:5]1([O:20][CH3:21])[CH2:10][CH2:9][N:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1>C(#N)C>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][C:5]1([O:20][CH3:21])[CH2:10][CH2:9][N:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]#[N:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 59186683HCID 59186683, compound

Product 1

HCID 59186704HCID 59186704, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of EXAMPLE 1F in acetonitrile (20 mL) at 0° C. was treated with DMF (0.543 mL, 7.02 mmol) and oxalyl chloride (0.561 mL, 6.43 mmol), stirred for 5 minutes, treated with pyridine (1.04 mL, 12.866 mmol), and stirred for another 50 minutes at 0° C. The reaction mixture was partitioned between ethyl acetate and saturated aqueous NaHCO3, the aqueous layer extracted with ethyl acetate three times and the combined organic layers dried (MgSO4), filtered, and concentrated to give the desired product as a residue that was utilized directly in the next step without further purification. MS (ESI) m/e 325 (M+H)+.

Workup

  1. stirringstirred for another 50 minutes at 0° C
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous NaHCO3
  3. extractionthe aqueous layer extracted with ethyl acetate three times
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f684a6bd98e641db8f7788a792a2dc67
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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