Sodium Hydroxide → HCID 68491522, compound

HRID 1879168Notes

Reaction equation

HRID 1879168 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[N:15][CH:14]=[C:13]([N:17]([CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH3:18])[N:12]=2)=[N:8][C:7]=1[CH3:29])=[O:5])C.[OH-].[Na+]>O1CCCC1>[F:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][CH2:19][N:17]([CH3:18])[C:13]2[N:12]=[C:11]([C:9]3[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:29])[N:8]=3)[CH:16]=[N:15][CH:14]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68488009HCID 68488009, compound

Product 1

HCID 68491522HCID 68491522, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part C. To a solution of 2-(6-{[2-(4-fluoro-phenoxy)-ethyl]-methyl-amino}-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (220 mg, 0.53 mmol) in tetrahydrofuran (8 mL) was added 1N NaOH (8 mL). The resulting reaction mixture was heated to reflux for 14 hr. The solvent was removed in vacuo, and the residue was neutralized to pH 4-5 with 10% HCl. The resulting precipitate was filtered and dried to afford 2-(6-{[2-(4-fluoro-phenoxy)-ethyl]-methyl-amino}-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid in 92% yield.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 14 hr
  4. customThe solvent was removed in vacuo
  5. filtrationThe resulting precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-bded2c0df0a0464c9c6a3cf9c927487c
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

Loading…