Benzenesulfonamide, N,4-dimethyl- → N-(6-(2-(N,4-dimethylphenylsulfonamido)pyridin-4-yl)benzo[d]thiazol-2-yl)acetamide

HRID 2077557Notes

Reaction equation

HRID 2077557 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].CC(C)([O-])C.[Na+].Cl[C:20]1[CH:25]=[C:24]([C:26]2[CH:38]=[CH:37][C:29]3[N:30]=[C:31]([NH:33][C:34](=[O:36])[CH3:35])[S:32][C:28]=3[CH:27]=2)[CH:23]=[CH:22][N:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][N:2]([C:20]1[CH:25]=[C:24]([C:26]2[CH:38]=[CH:37][C:29]3[N:30]=[C:31]([NH:33][C:34](=[O:36])[CH3:35])[S:32][C:28]=3[CH:27]=2)[CH:23]=[CH:22][N:21]=1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

7

Reactant 4

HCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 51354312HCID 51354312, compound

Product 1

HCID 57585098N-(6-(2-(N,4-dimethylphenylsulfonamido)pyridin-4-yl)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A microwave vial equipped with a stir bar was charged with n-methyl-p-toluenesulfonamide (0.26 g, 1.4 mmol) in DMF (3 ml). Then sodium t-butoxide (0.270 g, 2.8 mmol) was added to the mixture and allowed to stir 5 minutes. Then palladium(II) acetate (0.013 g, 0.057 mmol), N-(6-(2-chloropyridin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.173 g, 0.57 mmol) and Xantphos (0.010 g) was added to the mixture. The vial was capped and placed into a CEM Microwave for 20 minutes at 100° C., while 100 watts of energy was supplied via Powermax® (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed desired product peaks. The mixture was diluted with DMSO and purified by reverse-phase HPLC. This gave N-(6-(2-(N,4-dimethylphenylsulfonamido)pyridin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.010 g, 3.9% yield) as a tan solid. MS (ESI pos. ion) m/z: 453 (MH+). Calc'd exact mass for C22H20N4O3S2: 452. 1H NMR (300 MHz, DMSO-d6): 2.03 (s, 3H), 2.37 (s, 3H), 3.24 (s, 3H), 7.32-7.42 (d, 2H), 7.44-7.73 (m, 6H), 7.80 (s, 1H), 8.14 (s, 1H), 8.29 (d, 1H).

Workup

  1. customA microwave vial equipped with a stir bar
  2. customThe vial was capped
  3. waitplaced into a CEM Microwave for 20 minutes at 100° C., while 100 watts of energy
  4. temperaturewas supplied via Powermax® (Simultaneous heating while cooling technology)

Sources & evidence

ORD record
ord-ac7cec66b5874ff3bac3f7cf9464cd0e
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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