Water → HCID 19041641, compound

HRID 1684014Notes

Reaction equation

HRID 1684014 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])=[C:8]2[CH3:24])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.O>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH2:19][CH2:20][C:21]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)=[O:22])=[C:8]2[CH3:24])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 104392-AminopyridineHCID 65578Oxalyl chlorideHCID 19041674HCID 19041674, compound

Product 1

HCID 19041641HCID 19041641, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To the acid of Example 4, (400 mg, 0.96 mmol) in 30 mL CH2Cl2 at 0° C. was added a few drops of DMF followed by oxalyl chloride (100 μL, 1.15 mmol, dropwise). The reaction was stirred 15 min at 0° C., and then 2-amino pyridine (306 mg, 3.26 mmol) was added. The reaction mixture was stirred overnight at r.t., poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. Purification by flash chromatography (20%, ethyl acetate in hexane) provided 101 mg of the title compound as a yellow solid.

Workup

  1. stirringThe reaction mixture was stirred overnight at r.t.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customPurification by flash chromatography (20%, ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6f9a7429720c443fb2b9aff8df61fccc
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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