Benzenesulfonamide, N,4-dimethyl- → HCID 51354023, compound

HRID 2077511Notes

Reaction equation

HRID 2077511 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].[H-].[Na+].Cl[C:16]1[N:21]=[C:20]([C:22]2[CH:34]=[CH:33][C:25]3[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:24]=3[CH:23]=2)[CH:19]=[CH:18][N:17]=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.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][N:2]([C:16]1[N:21]=[C:20]([C:22]2[CH:34]=[CH:33][C:25]3[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:24]=3[CH:23]=2)[CH:19]=[CH:18][N:17]=1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

8

Reactant 4

HCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 24758Sodium hydrideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 51357685N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 51354023HCID 51354023, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A microwave vial equipped with a stir bar was charged with N-methyl-p-toluenesulfonamide (0.23 g, 1.2 mmol) in DMF (3 mL). NaH (0.12 g, 4.9 mmol) was added to the mixture and allowed to stir for 30 minutes. Then, palladium (II) acetate (0.011 g, 0.049 mmol), N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.150 g, 0.492 mmol), and Xantphos (0.010 g) were added to the mixture. The vial was capped and placed into a microwave for 10 minutes at 100° C. The mixture was then added to a RBF, diluted with water (150 mL), and allowed to stir overnight. The resulting precipitate was collected by filtration and washed with hexane and 1:1 hexanes/ethyl ether to provide N-(6-(2-(N,4-dimethylphenylsulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide as a tan solid. MS (ESI pos. ion) m/z: 454 (MH+). Calculated exact mass for C21H19N5O3S2: 453. 1H NMR (400 MHz, DMSO-d6): 12.52 (s, 1H), 8.64 (s, 1H), 8.48 (s, 1H), 8.10 (d, J=5.0 Hz, 1H), 7.93 (s, 2H), 7.83 (s, 1H), 7.71 (s, 1H), 7.40 (s, 2H), 3.70 (s, 3H), 2.37 (s, 3H), 2.24 (s, 3H).

Workup

  1. customA microwave vial equipped with a stir bar
  2. customThe vial was capped
  3. waitplaced into a microwave for 10 minutes at 100° C
  4. additionThe mixture was then added to a RBF
  5. stirringto stir overnight
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with hexane and 1:1 hexanes/ethyl ether

Sources & evidence

ORD record
ord-38834b4010b044729ac32f5959791dfc
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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