Trifluoroacetic acid → HCID 86682355, compound

HRID 2283603Notes

Reaction equation

HRID 2283603 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.C(OC(=O)[N:34]([S:40]([C:43]1[CH:48]=[C:47]([Cl:49])[C:46](F)=[CH:45][C:44]=1[F:51])(=[O:42])=[O:41])[C:35]1[N:36]=[CH:37][S:38][CH:39]=1)(C)(C)C.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:49][C:47]1[C:46]([O:27][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=2[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:45][C:44]([F:51])=[C:43]([S:40]([NH:34][C:35]2[N:36]=[CH:37][S:38][CH:39]=2)(=[O:41])=[O:42])[CH:48]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59436581Tert-butyl (5-chloro-2,4-difluorophenyl)sulfonyl(thiazol-4-yl)carbamateHCID 1357436831,1-Dimethylethyl 4-(4-(5-chloro-2-hydroxyphenyl)-2-pyrimidinyl)-1-piperazinecarboxylate

Product 1

HCID 86682355HCID 86682355, compoundYield 71.9%

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[(5-chloro-2,4-difluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate (Preparation 4, 43.6 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 mixture was diluted with water and the precipitate collected by filtration. The solid was dissolved in dichloromethane (2.0 mL) and dried over anhydrous magnesium sulfate. The mixture was filtered and trifluoroacetic acid (0.060 mL, 0.78 mmol) was added to the filtrate. After 2 hours the reaction mixture was concentrated in vacuo to a residue and purified by reverse phase HPLC to afford the title compound as a tan glass (55 mg).

Workup

  1. filtrationthe precipitate collected by filtration
  2. dissolutionThe solid was dissolved in dichloromethane (2.0 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe mixture was filtered
  5. concentrationAfter 2 hours the reaction mixture was concentrated in vacuo to a residue
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-2d49b795fbb748999ea56e1b2c234a6a
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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