Water → HCID 59520476, compound

HRID 1162785Notes

Reaction equation

HRID 1162785 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:7]([CH:8]=[O:9])=[CH:6][NH:5][N:4]=1.Cl[CH2:13][CH2:14][C:15]([NH:17][C:18]1[S:22][C:21]2[CH2:23][CH2:24][CH2:25][CH2:26][C:20]=2[C:19]=1[C:27]([NH:29][CH3:30])=[O:28])=[O:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[I-].[K+]>[CH:8]([C:7]1[C:3]([C:2]([F:1])([F:10])[F:11])=[N:4][N:5]([CH2:13][CH2:14][C:15]([NH:17][C:18]2[S:22][C:21]3[CH2:23][CH2:24][CH2:25][CH2:26][C:20]=3[C:19]=2[C:27]([NH:29][CH3:30])=[O:28])=[O:16])[CH:6]=1)=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 59520509HCID 59520509, compoundHCID 178519884HCID 178519884, compound

Product 1

HCID 59520476HCID 59520476, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde (437 mg, 2.66 mmol) and 2-(3-chloropropanamido)-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (801 mg, 2.66 mmol) were dissolved in DMF (15 mL). Potassium carbonate (368 mg, 2.66 mmol) was added followed by potassium iodide (10 mg, 0.06 mmol). The reaction mixture was left to stand for 7 days. Water was added and the reaction mixture extracted into EtOAc (×3). The EtOAc layers were combined and washed with water (×5), brine, dried over MgSO4, filtered and the solvent removed in vacuo to give desired product as a yellow solid (970 mg, 2.26 mmol, 85%).

Workup

  1. waitThe reaction mixture was left
  2. extractionthe reaction mixture extracted into EtOAc (×3)
  3. washwashed with water (×5), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6a649ba15a874ff8b729c84934ea087a
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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