1,4-Dioxane → 5-(4-tert-butylthiazol-2-ylamino)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)pyridine-2-sulfonamide

HRID 1644665Notes

Reaction equation

HRID 1644665 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:4]=1[CH2:5][N:6]([C:17]1[S:18][CH:19]=[CH:20][N:21]=1)[S:7]([C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][N:11]=1)(=[O:9])=[O:8].CC(C)([O-])C.[Na+].[CH3:34][C:35]1([CH3:75])[C:48]2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)[C:43]=2OC2[C:36]1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:76][C:77]1[S:78]C=C(C2C=CC(Cl)=CC=2)[N:81]=1.O1CCOCC1>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]>[C:35]([C:48]1[N:76]=[C:77]([NH:81][C:13]2[CH:14]=[CH:15][C:10]([S:7]([N:6]([CH2:5][C:4]3[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:3]=3[O:2][CH3:1])[C:17]3[S:18][CH:19]=[CH:20][N:21]=3)(=[O:9])=[O:8])=[N:11][CH:12]=2)[S:78][CH:43]=1)([CH3:75])([CH3:36])[CH3:34]

Participants

7

Reactant 5

HCID 312751,4-DioxaneHCID 732412-Amino-4-(4-chlorophenyl)thiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 57551263N-(2,4-dimethoxybenzyl)-5-iodo-N-(thiazol-2-yl)pyridine-2-sulfonamide

Product 1

HCID 575512625-(4-tert-butylthiazol-2-ylamino)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)pyridine-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
150 °C

Procedure

Into a Vial was added the 5-Iodo-pyridine-2-sulfonic acid (2,4-dimethoxy-benzyl)-thiazol-2-yl-amide (80 mg, 0.0001 mol), Sodium tert-butoxide (43 mg, 0.00044 mol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (1.0E1 mg, 0.000018 mol), Tris(dibenzylideneacetone)dipalladium(0) (5.4 mg, 0.0000059 mol), 2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE and the de-gassed anhydrous 1,4-Dioxane (2.0 mL, 0.026 mol). The reaction mixture was heated at 150° C. for 1 h in microwave. The reaction mixture was filtered through Celite and the filtrate was concentrated to give the crude product that was purified on ISCO twice (10% to 100% E/H) to give the product as a light brown solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product that
  4. customwas purified on ISCO twice (10% to 100% E/H)

Sources & evidence

ORD record
ord-94b6ffa27ce34f719937bb102bc66de9
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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