Methanesulfonamide → HCID 56602986, compound

HRID 1620311Notes

Reaction equation

HRID 1620311 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[C:15]([C:16]3[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=3)=[CH:14][C:10]([C:11](O)=[O:12])=[C:9]([F:24])[CH:8]=2)=[C:4]([O:27][CH3:28])[CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:62][S:63]([NH2:66])(=[O:65])=[O:64]>C(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[C:15]([C:16]3[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=3)=[CH:14][C:10]([C:11]([NH:66][S:63]([CH3:62])(=[O:65])=[O:64])=[O:12])=[C:9]([F:24])[CH:8]=2)=[C:4]([O:27][CH3:28])[CH:3]=1

Participants

7

Reactant 4

HCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66667694HCID 66667694, compound

Product 1

HCID 56602986HCID 56602986, compoundYield 113.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-chloro-2-methoxyphenoxy)-2-fluoro-5-(2-methoxypyridin-3-yl)benzoic acid (Preparation 15, 0.070 g, 0.114 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.112 g, 0.294 mmol) and N,N-diisopropylethylamine (191 μL, 1.09 mmol) in DCM (10 mL) and dimethylformamide (1.1 mL) was stirred at room temperature for 10 minutes, then methyl sulfonamide (0.0397 g, 0.417 mmol) was added. The reaction was heated at 45° C. for 18 hours under a nitrogen atmosphere, then cooled to room temperature and concentrated in vacuo to afford a pale brown residue. This was partitioned between aqueous hydrochloric acid (0.5 M, 10 mL) and DCM (25 mL). The organic extract was washed with aqueous hydrochloric acid (0.5 M, 2×10 mL), dried over sodium sulfate and concentrated in vacuo to afford a pale brown gum (0.062 g). The crude product was purified by preparative A-HPLC to afford the title compound (26.7 mg):

Workup

  1. temperatureThe reaction was heated at 45° C. for 18 hours under a nitrogen atmosphere
  2. temperaturecooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customto afford a pale brown residue
  5. customThis was partitioned between aqueous hydrochloric acid (0.5 M, 10 mL) and DCM (25 mL)
  6. extractionThe organic extract
  7. washwas washed with aqueous hydrochloric acid (0.5 M, 2×10 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3927d2d5cef4ababd8a118521de21b9
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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