Cyclohexylamine → HCID 86704195, compound

HRID 1497656Notes

Reaction equation

HRID 1497656 reaction equation
Br[C:2]1[S:3][C:4]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[C:5]([C:7]2[C:8]([F:29])=[C:9]([N:14]([CH2:26][O:27][CH3:28])[S:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])(=[O:17])=[O:16])[CH:10]=[CH:11][C:12]=2[F:13])[N:6]=1.[CH:36]1([NH2:42])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>CC(N(C)C)=O>[CH:36]1([NH:42][C:2]2[S:3][C:4]([C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)=[C:5]([C:7]3[C:8]([F:29])=[C:9]([N:14]([CH2:26][O:27][CH3:28])[S:15]([C:18]4[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=4[F:25])(=[O:17])=[O:16])[CH:10]=[CH:11][C:12]=3[F:13])[N:6]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 86704196HCID 86704196, compound

Product 1

HCID 86704195HCID 86704195, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

N-{3-[2-bromo-5-(pyridin-4-yl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide (prepared as described in Example 3, 50 mg, 0.09 mmol) was dissolved in 3 mL of dimethylacetamide and 74 μL (0.85 mmol) of cyclohexylamine were added. The mixture was stirred at 110° C. for 16 h. The solvent was evaporated under reduced pressure and the residue was taken up with DCM and washed with brine. The organic layer was dried over Na2SO4 and evaporated, giving N-{3-[2-(cyclohexylamino)-5-(pyridin-4-yl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide. The latter, without any further purification, was treated with 4 mL of TFA and 1 mL of water and stirred at 75° C. for 8 h. The solvent was then removed, the residue taken up with DCM and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and evaporated. The crude was purified by flash chromatography eluted with cyclohexane-ethanol 9/1, affording 20 mg (42%) of the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-07cc255a27894749b0b23e6bc332ab91
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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