Trifluoroacetic acid → 3'-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid amide

HRID 1928151Notes

Reaction equation

HRID 1928151 reaction equation
C([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[CH:24]=[C:23]([CH3:34])[N:22]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([C:25]2[CH:24]=[C:23]([CH3:34])[N:22]=[C:21]([C:17]3[CH:16]=[C:15]([C:11]4[CH:12]=[CH:13][CH:14]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:10]=4)[CH:20]=[CH:19][CH:18]=3)[N:26]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 602094263'-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide

Product 1

HCID 574688963'-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid amideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of 3′-[4-(4-chloro-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide (0.16 g) in dichloromethane (3 mL) was added TFA (3 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 to yield the title compound as an off-white solid (0.083, 63%). MS (ISP) 436.1 [(M+H)+]; mp 221° 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

Sources & evidence

ORD record
ord-184de579982d4de6aa68cd9ccfe5f073
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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