Trifluoroacetic acid → HCID 86682357, compound

HRID 2283604Notes

Reaction equation

HRID 2283604 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.[Cl:28][C:29]1[C:30](F)=[CH:31][C:32]([F:55])=[C:33]([S:35]([N:38](CC2C=CC(OC)=CC=2OC)[C:39]2[S:40][CH:41]=[N:42][N:43]=2)(=[O:37])=[O:36])[CH:34]=1.C(=O)([O-])[O-].[K+].[K+].[F:63][C:64]([F:69])([F:68])[C:65]([OH:67])=[O:66]>CS(C)=O.O>[F:63][C:64]([F:69])([F:68])[C:65]([OH:67])=[O:66].[Cl:28][C:29]1[C:30]([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:31][C:32]([F:55])=[C:33]([S:35]([NH:38][C:39]2[S:40][CH:41]=[N:42][N:43]=2)(=[O:36])=[O:37])[CH:34]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 1357436831,1-Dimethylethyl 4-(4-(5-chloro-2-hydroxyphenyl)-2-pyrimidinyl)-1-piperazinecarboxylate

Product 1

HCID 86682357HCID 86682357, compoundYield 46.3%

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), 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 6, 49.1 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 (35.5 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-0ab54e4639714c8ab43a7a71ddb894ee
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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