Dimethylacetamide → 5-(1-(4-chlorobenzyl)-1H-pyrazol-4-ylamino)-N-(thiazol-2-yl)pyridine-2-sulfonamide

HRID 1644669Notes

Reaction equation

HRID 1644669 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.[Cl:59][C:60]1[CH:72]=[CH:71][C:63]([CH2:64][N:65]2[CH:69]=[C:68]([NH2:70])[CH:67]=[N:66]2)=[CH:62][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]>[Cl:59][C:60]1[CH:72]=[CH:71][C:63]([CH2:64][N:65]2[CH:69]=[C:68]([NH:70][C:13]3[CH:14]=[CH:15][C:10]([S:7]([NH:6][C:2]4[S:1][CH:5]=[CH:4][N:3]=4)(=[O:9])=[O:8])=[N:11][CH:12]=3)[CH:67]=[N:66]2)=[CH:62][CH:61]=1

Participants

7

Reactant 5

HCID 31374DimethylacetamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 6736891-[(4-Chlorophenyl)methyl]-1h-pyrazol-4-amineHCID 23676156Sodium t-butoxideHCID 575512525-bromo-N-(thiazol-2-yl)pyridine-2-sulfonamide

Product 1

HCID 575512695-(1-(4-chlorobenzyl)-1H-pyrazol-4-ylamino)-N-(thiazol-2-yl)pyridine-2-sulfonamideYield 19.8%

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 (50 mg, 0.0002 mol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (11 mg, 0.000019 mol), Tris(dibenzylideneacetone)dipalladium(0) (5.7 mg, 0.0000062 mol), 1-(4-Chloro-benzyl)-1H-pyrazol-4-ylamine (39 mg, 0.00019 mol) and N,N-Dimethylacetamide (2.1 mL, 0.022 mol). The mixture was sparged with argon for ˜5 min. Sodium tert-butoxide (75 mg, 0.00078 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 (40% to 100% Ethyl acetate). 16.8 mg of the product was obtained as a light tan 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 (40% to 100% Ethyl acetate)

Sources & evidence

ORD record
ord-320d67d579f14d84a21d010642fa7835
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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