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

HRID 2077505Notes

Reaction equation

HRID 2077505 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:40]=[CH:39][C:31]3[N:32]=[C:33]([NH:35][C:36](=[O:38])[CH3:37])[S:34][C:30]=3[CH:29]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(Cl)Cl.C([O-])(O)=O.[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][N:8]([C:6]1[N:7]=[C:2]([C:28]2[CH:40]=[CH:39][C:31]3[N:32]=[C:33]([NH:35][C:36](=[O:38])[CH3:37])[S:34][C:30]=3[CH:29]=2)[CH:3]=[CH:4][CH:5]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamideHCID 57585115N-(6-chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamide

Product 1

HCID 25183328N-(6-(6-(N,4-dimethylphenylsulfonamido)pyridin-2-yl)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
95 °C

Procedure

N-(6-Chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamide (0.080 g, 0.27 mmol) was dissolved in 1,4-dioxane (6 mL), and N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.1 g, 0.3 mmol), tetrakis(triphenylphosphine)palladium (0) (0.04 g, 0.04 mmol) and 2M Na2CO3 (0.3 mL, 0.6 mmol) were added to the mixture. The flask was fit with a reflux condensor and placed into a pre-heated (95° C.) bath and stirred under an inert atmosphere overnight. The mixture was then allowed to cool to ambient temperature and diluted with DCM and saturated NaHCO3. The organic layers were collected by extracting with DCM three times, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude was purified by silica gel chromatography (1-10% IPA/DCM) to give N-(6-(6-(N,4-dimethylphenylsulfonamido)pyridin-2-yl)benzo[d]thiazol-2-yl)acetamide as a tan solid. MS (ESI pos. ion) m/z: 453 (MH+). Calculated exact mass for C22H20N4O3S2: 452. 1H NMR (400 MHz, DMSO-d6): 8.35 (s, 1H), 7.93 (t, J=8.0 Hz, 2H), 7.83 (d, J=7.5 Hz, 1H), 7.74 (d, J=8.5 Hz, 1H), 7.58 (d, J=8.0 Hz, 2H), 7.48 (d, J=8.0 Hz, 1H), 7.37 (d, J=7.5 Hz, 2H), 3.38 (s, 3H), 2.36 (s, 3H), 2.22 (s, 3H).

Workup

  1. temperatureto cool to ambient temperature
  2. customThe organic layers were collected
  3. extractionby extracting with DCM three times
  4. dry with materialthe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by silica gel chromatography (1-10% IPA/DCM)

Sources & evidence

ORD record
ord-c907512aaa2340da879f3b87e392bf63
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

Loading…