Sodium Carbonate → HCID 57584970, compound

HRID 2077501Notes

Reaction equation

HRID 2077501 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OC([C:26]2[CH:38]=[CH:37][C:29]3[N:30]=[C:31]([NH:33]C(=O)C)[S:32][C:28]=3[CH:27]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[NH2:33][C:31]1[S:32][C:28]2[CH:27]=[C:26]([C:2]3[N:7]=[C:6]([NH:8][S:9]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)(=[O:11])=[O:10])[CH:5]=[CH:4][CH:3]=3)[CH:38]=[CH:37][C:29]=2[N:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 57585043HCID 57585043, compoundHCID 57585045HCID 57585045, compound

Product 1

HCID 57584970HCID 57584970, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

N-(6-Chloropyridin-2-yl)benzenesulfonamide (0.480 g, 1.90 mmol) was dissolved in 1,4-dioxane (6 mL). Then N-(6-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.7 g, 2 mmol), 2M Na2CO3 (2 mL, 4 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.3 g, 0.2 mmol) was added to the mixture. The flask was fit with a reflux condensor, then placed into a pre-heated (95° C.) bath and allowed to stir under inert atmosphere overnight. The flask was removed from the heat bath and allowed to cool to ambient temperature. The mixture was filtered through a fritted funnel and the crude filtrate was purified by reverse-phase HPLC. This gave N-(6-(2-aminobenzo[d]thiazol-6-yl)pyridin-2-yl)benzenesulfonamide. MS (ESI pos. ion) m/z: 383 (MH+). Calculated exact mass for C18H14N4O2S2: 382. 1H NMR (400 MHz, acetone-d6): 8.19 (s, 1H), 8.08 (d, J=8.0 Hz, 2H), 7.86 (d, J=8.0 Hz, 1H), 7.74 (t, J=8.0 Hz, 1H), 7.53-7.64 (m, 4H), 7.44 (d, J=8.5 Hz, 1H), 7.13 (d, J=8.0 Hz, 1H), 6.98 (br s, 1H).

Workup

  1. customThe flask was removed from the heat bath
  2. temperatureto cool to ambient temperature
  3. filtrationThe mixture was filtered through a fritted funnel
  4. customthe crude filtrate was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-a777eac0385d4b1ba1e5661b83cac77d
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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