Potassium Carbonate → HCID 86682366, compound

HRID 2283615Notes

Reaction equation

HRID 2283615 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:8]=2[OH:18])=[CH:3][N:2]=1.[C:19](=O)([O-:21])[O-:20].[K+].[K+].C(OC(=O)[N:31]([S:37]([C:40]1[CH:45]=[C:44]([Cl:46])[C:43](F)=[CH:42][C:41]=1[F:48])(=[O:39])=[O:38])[C:32]1[N:33]=[CH:34][S:35][CH:36]=1)(C)(C)C>CS(C)=O.O>[F:17][C:14]([F:15])([F:16])[C:19]([OH:21])=[O:20].[Cl:46][C:44]1[C:43]([O:18][C:8]2[CH:9]=[CH:10][C:11]([O:13][C:14]([F:16])([F:17])[F:15])=[CH:12][C:7]=2[C:4]2[CH:5]=[CH:6][N:1]=[N:2][CH:3]=2)=[CH:42][C:41]([F:48])=[C:40]([S:37]([NH:31][C:32]2[N:33]=[CH:34][S:35][CH:36]=2)(=[O:38])=[O:39])[CH:45]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59436581Tert-butyl (5-chloro-2,4-difluorophenyl)sulfonyl(thiazol-4-yl)carbamateHCID 1360636182-Pyridazin-4-yl-4-(trifluoromethoxy)phenol

Product 1

HCID 86682366HCID 86682366, compoundYield 118.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-Pyridazin-4-yl-4-(trifluoromethoxy)phenol (Preparation 30, 88 mg, 0.34 mmol) was dissolved in dimethylsulfoxide (4 mL). Potassium carbonate (90 mg, 0.65 mmol) was added, followed by tert-butyl[(5-chloro-2,4-difluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate (Preparation 4, 141 mg, 0.34 mmol). The reaction mixture was stirred for 18 hours at ambient temperature then diluted with water and extracted with ethyl ether (×3). The combined organic phase was concentrated in vacuo and purified by silica gel column chromatography (hexanes to ethyl acetate gradient elution). The residue was dissolved in saturated hydrogen chloride in methanol and stirred for 18 hours at ambient temperature. The reaction mixture was concentrated in vacuo and purified by reverse phase HPLC to afford the title compound as an off-white powder (133 mg).

Workup

  1. extractionextracted with ethyl ether (×3)
  2. concentrationThe combined organic phase was concentrated in vacuo
  3. custompurified by silica gel column chromatography (hexanes to ethyl acetate gradient elution)
  4. dissolutionThe residue was dissolved in saturated hydrogen chloride in methanol
  5. stirringstirred for 18 hours at ambient temperature
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-d7221134127f48c1a403aa0d60077b0c
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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