Trifluoroacetic acid → HCID 86682368, compound

HRID 2283619Notes

Reaction equation

HRID 2283619 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:27])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[N:9]=2)[CH:7]=1.[S:28]1[CH:32]=[C:31]([N:33]([S:41]([C:44]2[CH:49]=[C:48]([F:50])[C:47](F)=[CH:46][C:45]=2[F:52])(=[O:43])=[O:42])C(=O)OC(C)(C)C)[N:30]=[CH:29]1.C(=O)([O-])[O-].[K+].[K+].[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62]>CS(C)=O.O>[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][C:47]2[C:48]([F:50])=[CH:49][C:44]([S:41]([NH:33][C:31]3[N:30]=[CH:29][S:28][CH:32]=3)(=[O:43])=[O:42])=[C:45]([F:52])[CH:46]=2)=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[N:9]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59436528tert-Butyl 1,3-thiazol-4-yl[(2,4,5-trifluorophenyl)sulfonyl]carbamateHCID 1357436831,1-Dimethylethyl 4-(4-(5-chloro-2-hydroxyphenyl)-2-pyrimidinyl)-1-piperazinecarboxylate

Product 1

HCID 86682368HCID 86682368, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

tert-Butyl 4-[4-(5-chloro-2-hydroxyphenyl)pyrimidin-2-yl]piperazine-1-carboxylate (Preparation 2, 48.6 mg, 0.11 mmol), tert-butyl 1,3-thiazol-4-yl[(2,4,5-trifluorophenyl)sulfonyl]carbamate (Preparation 45, 41.9 mg, 0.11 mmol) and potassium carbonate (21.9 mg, 0.16 mmol) were mixed in dimethylsulfoxide (1 mL) and shaken at ambient temperature for 18 hours. The reaction was diluted with water and the precipitate collected by filtration. The solid was dissolved in dichloromethane (2 mL), and dried over anhydrous magnesium sulfate. The mixture was filtered and trifluoroacetic acid (0.06 mL, 0.78 mmol) was added to the filtrate. After 2 hours the reaction was concentrated in-vacuo and purified by reverse phase HPLC to afford the title compound as a tan glass (52 mg).

Workup

  1. filtrationthe precipitate collected by filtration
  2. dissolutionThe solid was dissolved in dichloromethane (2 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe mixture was filtered
  5. concentrationAfter 2 hours the reaction was concentrated in-vacuo
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-ae31e3e99c5d45349ca7bc1e65b0db81
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

Loading…