4-(Trifluoromethyl)benzenesulfonyl chloride → HCID 23446677, compound

HRID 1841613Notes

Reaction equation

HRID 1841613 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]1[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.[F:16][C:17]([F:29])([F:28])[C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[CH3:15][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]1[CH:9]=[N:10][C:11]([NH:14][S:24]([C:21]2[CH:20]=[CH:19][C:18]([C:17]([F:16])([F:28])[F:29])=[CH:23][CH:22]=2)(=[O:26])=[O:25])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 23446450HCID 23446450, compound

Product 1

HCID 23446677HCID 23446677, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 102 mg (0.5 mmol) of 5-(5-Dimethylamino-pent-1-ynyl)-pyrimidin-2-ylamine in 3.9 ml pyridine was treated with 257 mg (1.05 mmol) 4-(trifluoromethyl)benzenesulfonyl chloride. The reaction was stirred over night at 70° C., evaporated and extracted with aqueous saturated NaHCO3(2×)/CH2Cl2 (3×). The organic phases were washed with aqueous 10% NaCl solution, dried (Na2SO4) and evaporated. Flash column chromatography on silica gel with CH2Cl2/MeOH (95:5 to 9:1) yielded 70 mg (34%) of N-[5-(5-Dimethylamino-pent-1-ynyl)-pyrimidin-2-yl]-4-trifluoromethyl-benzenesulfonamide, mp: 194-202° C.,slowly dec.; MS: 413 (MH+).

Workup

  1. customevaporated
  2. extractionextracted with aqueous saturated NaHCO3(2×)/CH2Cl2 (3×)
  3. washThe organic phases were washed with aqueous 10% NaCl solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-46da36073259499fb04e885f1a8a17c5
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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