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Morpholine → N-(4-Chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-3-fluoro-4-morpholin-4-yl-benzenesulfonamide

HRID 218206
Notes
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Reaction equation

HRID 218206 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[N:19]2[C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[N:20]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:28].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:3]([F:28])[CH:4]=2)(=[O:10])=[O:9])=[C:13]([N:19]2[C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[N:20]2)[CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8083MorpholineHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 59428112HCID 59428112, compound

Product 1

HCID 25134398N-(4-Chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-3-fluoro-4-morpholin-4-yl-benzenesulfonamideYield 44.2%

Reagents, catalysts & solvents 2

HCID 9832798
Tris(dibenzylideneacetone) dipalladium
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-3-fluoro-benzensulfonamide (synthesized according to general procedure G, 180 mg, 0.37 mmol) was dissolved in 3 ml of anhydrous dimethylformamide under an atmosphere of nitrogen. To this mixture was added morpholine (161 mg, 1.85 mmol), 2,2′-bis(diphenylphosphine)-1,1′-binaphthyl (BINAP) (34 mg, 0.055 mmol), potassium phosphate tribasic monohydrate (511 mg, 2.22 mmol), and tris(dibenzylideneacetone) dipalladium(0) (Pd2(dba)3) and the resultant mixture was heated at 80° C. overnight. The following day, the reaction mixture was partitioned with a saturated solution of sodium bicarbonate and dichloromethane and the aqueous layer was extracted three times with dichloromethane. The combined organics were subsequently dried over magnesium sulfate, concentrated in vacuo, and purified by reverse phase HPLC, followed by silica gel chromatography employing ethyl acetate:hexanes (1:1), to afford 80 mg of the desired product as a white powder: MS (ES) M+H expected 489.1, found 489.0.

Workup

  1. customThe following day, the reaction mixture was partitioned with a saturated solution of sodium bicarbonate and dichloromethane
  2. extractionthe aqueous layer was extracted three times with dichloromethane
  3. dry with materialThe combined organics were subsequently dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-7626c644499c4338a1dd06ea6956c4c2
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08198309B2

Reaction notes

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