Pyridine → HCID 58174062, compound

HRID 1255906Notes

Reaction equation

HRID 1255906 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[N:8]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][N:16]=2)[C:11]([NH:18][CH2:19][CH2:20][C:21]2C=C[C:24]([O:28][C:29]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]=3)=[C:25](O)[CH:26]=2)=[N:10][CH:9]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N:8]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][N:16]=2)[C:11]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:28][C:29]3[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[CH:31][N:30]=3)=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)=[N:10][CH:9]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 58174106HCID 58174106, compound

Product 1

HCID 58174062HCID 58174062, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 4 mL of acetic anhydride was added 5-[2-(Pteridin-4-ylamino)-ethyl]-2-(4-trifluoromethylpyridin-2-yloxy)-phenol (330 mg, 0.7 mmol), pyridine (0.5 mL), and 5 mg DMAP. The solution was stirred at ambient temperature for 15 h, then diluted with CH2Cl2 and washed sequentially with H2O and saturated aqueous NaHCO3 solution. The organic fraction was dried with Na2SO4, suction filtered, and concentrated in vacuo. The residue was diluted with 1:1 Et2O/pentane. The product precipitated, was collected by filtration, and the cake washed with cool 1:1 Et2O/pentane. This afforded 184 mg (56% yield) of acetic acid 5-[2-(pteridin-4-ylamino)-ethyl]-2-(4-trifluoromethylpyridin-2-yloxy)-phenyl ester, an off-white solid: ESIMS m/z: 471 ([M]).

Workup

  1. washwashed sequentially with H2O and saturated aqueous NaHCO3 solution
  2. dry with materialThe organic fraction was dried with Na2SO4, suction
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with 1:1 Et2O/pentane
  6. customThe product precipitated
  7. filtrationwas collected by filtration
  8. washthe cake washed
  9. temperaturewith cool 1:1 Et2O/pentane

Sources & evidence

ORD record
ord-68f4fdd44fce4e8e80445990aef78f51
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Reaction notes

Loading…