Dimethylacetamide → 5-(3-methyl-1-phenyl-1H-pyrazol-5-ylamino)-N-(thiazol-2-yl)pyridine-2-sulfonamide

HRID 1644670Notes

Reaction equation

HRID 1644670 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][N:11]=1)(=[O:9])=[O:8].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:59][C:60]1[N:64]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[N:63]=[C:62]([CH3:71])[CH:61]=1.CN(C)C(=O)C.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:71][C:62]1[CH:61]=[C:60]([NH:59][C:13]2[CH:14]=[CH:15][C:10]([S:7]([NH:6][C:2]3[S:1][CH:5]=[CH:4][N:3]=3)(=[O:9])=[O:8])=[N:11][CH:12]=2)[N:64]([C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)[N:63]=1

Participants

7

Reactant 5

HCID 31374DimethylacetamideHCID 708015-Amino-3-methyl-1-phenylpyrazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 575512525-bromo-N-(thiazol-2-yl)pyridine-2-sulfonamide

Product 1

HCID 575512055-(3-methyl-1-phenyl-1H-pyrazol-5-ylamino)-N-(thiazol-2-yl)pyridine-2-sulfonamideYield 61.1%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

Into a Vial was added the 5-Bromo-pyridine-2-sulfonic acid thiazol-2-ylamide (75 mg, 0.00023 mol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (16 mg, 0.000028 mol), Tris(dibenzylideneacetone)dipalladium(0) (8.6 mg, 0.0000094 mol), 5-AMINO-3-METHYL-1-PHENYLPYRAZOLE (49 mg, 0.00028 mol) and N,N-Dimethylacetamide (3.0 mL, 0.032 mol). The mixture was sparged with argon for ˜5 min. Sodium tert-butoxide (68 mg, 0.00070 mol) was added and the reaction mixture was heated at 120° C. for 30 min in microwave. The reaction mixture was filtered through celite. The filtrate was diluted with Ethyl acetate and washed with 0.1 N HCl solution, water (3×) and brine, dried over sodium sulfate, filtered and was concentrated to give the crude product that was purified on ISCO (0% to 100% Ethyl acetate in CHCl3). 58 mg of the product was obtained as a light brown solid.

Workup

  1. customThe mixture was sparged with argon for ˜5 min
  2. filtrationThe reaction mixture was filtered through celite
  3. additionThe filtrate was diluted with Ethyl acetate
  4. washwashed with 0.1 N HCl solution, water (3×) and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationwas concentrated
  8. customto give the crude product that
  9. customwas purified on ISCO (0% to 100% Ethyl acetate in CHCl3)

Sources & evidence

ORD record
ord-63bae1d860a74e9c8e7f0ceb65e116df
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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