Dichloromethane → HCID 57468950, compound

HRID 1928206Notes

Reaction equation

HRID 1928206 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[CH:19]=[C:18]([C:20]3[N:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=4Cl)[CH:23]=[C:22]([CH3:34])[N:21]=3)[CH:17]=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.[Cl:42]CCl>>[Cl:42][C:28]1[CH:27]=[C:26]([C:24]2[CH:23]=[C:22]([CH3:34])[N:21]=[C:20]([C:18]3[CH:17]=[CH:16][N:15]=[C:14]([C:11]4[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=4)[CH:19]=3)[N:25]=2)[CH:31]=[CH:30][C:29]=1[Cl:32]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 60209440HCID 60209440, compound

Product 1

HCID 57468950HCID 57468950, compoundYield 5%

Procedure

To a cooled and stirred solution of 5-{4-[4-(2,4-dichloro-phenyl)-6-methyl-pyrimidin-2-yl]-pyridin-2-yl}-thiophene-2-sulfonic acid tert-butylamide (0.22 g) in dichloromethane (6 mL) was added TFA (6 mL) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness and saturated NaHCO3 solution (5 mL), diethyl ether and heptane were added. The mixture was stirred at room temperature for 1 h, the precipitate was collected by filtration, washed with water and heptane and dried. Further purification by flash-chromatography on silica gel (ethyl acetate/hexane) and crystallization (dichloromethane) yielded the title compound as a white solid (0.024 g, 5%). MS (ISP) 477.1 [(M+H)+]; mp 267° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (5 mL), diethyl ether and heptane
  3. additionwere added
  4. stirringThe mixture was stirred at room temperature for 1 h
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water and heptane
  7. customdried
  8. customFurther purification by flash-chromatography
  9. customon silica gel (ethyl acetate/hexane) and crystallization (dichloromethane)

Sources & evidence

ORD record
ord-75df0a851d864aab8180d553e6a26ab4
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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