Water → HCID 59526152, compound

HRID 386131Notes

Reaction equation

HRID 386131 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([F:12])[C:3]=1[C:13]1[S:17][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22](=[O:25])[NH:21][N:20]=2)=[C:15]([C:26]([NH2:28])=[O:27])[CH:14]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38].O>CN(C=O)C>[CH3:40][O:39][C:37](=[O:38])[CH2:36][N:21]1[C:22](=[O:25])[CH:23]=[CH:24][C:19]([NH:18][C:16]2[S:17][C:13]([C:3]3[C:2]([F:1])=[CH:7][C:6]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:5][C:4]=3[F:12])=[CH:14][C:15]=2[C:26]([NH2:28])=[O:27])=[N:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 59526009HCID 59526009, compound

Product 1

HCID 59526152HCID 59526152, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-oxo-1,6-dihydropyridazin-3-yl)amino]thiophene-3-carboxamide (Example 578 Step 3) (50 mg, 0.12 mmol), K2CO3 (18.70 mg, 0.14 mmol) and methyl bromoacetate (0.012 mL, 0.13 mmol) were stirred in DMF (1 mL) at 80° C. overnight. The reaction mixture was cooled to room temperature, water was added and the reaction mixture was extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (0-15% MeOH—CHCl3) gave the title compound as a yellow solid after triturating in DCM.

Workup

  1. extractionthe reaction mixture was extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by silica gel column chromatography (0-15% MeOH—CHCl3)

Sources & evidence

ORD record
ord-a62e55b8ec07420e87886a4f2b09a83e
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…