Trifluoroacetic acid → HCID 11602586, compound

HRID 2219579Notes

Reaction equation

HRID 2219579 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[N:9]=[C:10]([NH:13][C:14]([C:16]2[C:21]([NH:22][C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)=[CH:20][CH:19]=[C:18]([CH3:29])[N:17]=2)=[O:15])[S:11][CH:12]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[OH:6][CH2:7][C:8]1[N:9]=[C:10]([NH:13][C:14]([C:16]2[C:21]([NH:22][C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)=[CH:20][CH:19]=[C:18]([CH3:29])[N:17]=2)=[O:15])[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 131726997HCID 131726997, compound

Product 1

HCID 11602586HCID 11602586, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 40 mg (0.088 mmol) of 6-Methyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid [4-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-2-yl]-amide in 1 ml of methylene chloride was added 200 mg (1.75 mmol, 20.0 equiv.) of Trifluoroacetic acid. After stirring for 2 h at room temperature, saturated sodium carbonate solution was added, and the pH was adjusted to 8. The aqueous phase was extracted three times with methylene chloride. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vaccuo. The residue (28 mg, yellow solid) was triturated with Diisopropyl ether, filtered and dried to yield the title compound (17 mg, 57%) as a light yellow solid, MS (ISP): m/e=343.1 (M+H+).

Workup

  1. extractionThe aqueous phase was extracted three times with methylene chloride
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vaccuo
  5. customThe residue (28 mg, yellow solid) was triturated with Diisopropyl ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-82b7ea0e657246d7aa5a8bbe1e62b86f
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

Loading…