Sodium Iodide → HCID 178428226, compound

HRID 1042085Notes

Reaction equation

HRID 1042085 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[N:19]=[C:18](Cl)[CH:17]=[C:16]([Cl:21])[N:15]=2)=[CH:9][CH:8]=1)=[O:5].[CH3:27][C:28]1[CH:29]=[C:30]([NH2:33])[NH:31][N:32]=1.[I-].[Na+].C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.CN(C)C=O>[F:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([S:13][C:14]2[N:15]=[C:16]([Cl:21])[CH:17]=[C:18]([NH:33][C:30]3[NH:31][N:32]=[C:28]([CH3:27])[CH:29]=3)[N:19]=2)=[CH:11][CH:12]=1)=[O:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 594208272,6-Difluoro-N-[4-(4,6-dichloro-pyrimidin-2-ylsulfanyl)-phenyl]-benzamideHCID 178418690HCID 178418690, compound

Product 1

HCID 178428226HCID 178428226, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A 50 ml round bottom flask was charged with 2,6-difluoro-N-[4-(4,6-dichloro-pyrimidin-2-ylsulfanyl)-phenyl]-benzamide (1.0 g, 2.3 mmol), 5-methyl-2H-pyrazol-3-ylamine (250 mg, 2.58 mmol), sodium iodide (351 mg, 2.34 mmol), diisopropylethyl amine (333 mg, 2.58 mmol) and dimethylformamide (5 ml) under nitrogen. The reaction mixture was stirred at 90° C. for 18 h, then allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate (25 ml), washed with saturated sodium bicarbonate solution and brine. The organic was dried over magnesium sulfate, filtered and concentrated in vacuo. The compound was purified by flash chromatography (75 to 80% ethyl acetate/petrol) to give the title compound (1.08 g, 98%). 1H NMR (DMSO) 2.00 (3H, s), 5.25 (1H, brs), 6.48 (1H, brs), 7.30-7.97 (7H, m), 10.28 (1H, s), 10.89 (1H, s), 11.90 (1H, s); MS (ES+): 473.4.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialThe organic was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe compound was purified by flash chromatography (75 to 80% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-f3b537468ae04652943c902f8697999f
Source dataset
uspto-grants-2013_10
Patent number
US08557833B2

Reaction notes

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