Cesium carbonate → HCID 49806493, compound

HRID 2387771Notes

Reaction equation

HRID 2387771 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]3[N:13]=[C:14]([NH2:16])[S:15][C:11]=3[CH:10]=2)[CH:6]=[N:7][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1>CC(N(C)C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]3[N:13]=[C:14]([NH:16][C:26]4[CH:31]=[N:30][CH:29]=[CH:28][N:27]=4)[S:15][C:11]=3[CH:10]=2)[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 73277ChloropyrazineHCID 86761618HCID 86761618, compound

Product 1

HCID 49806493HCID 49806493, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
200 °C

Procedure

As shown in step 8-iii of Scheme 8, of 6-(5-methoxypyridin-3-yl)benzo[d]thiazol-2-amine (250 mg; 0.97 mmol) was dissolved in 4.0 mL of dry DMA. Cesium carbonate (650 mg; 2.0 mmol] and 2-chloropyrazine (Aldrich Chemical Co. Cat. No. 13, 248-9, 250 mg; 2.35 mmol) were added and the mixture heated in a sealed tube under microwave irradiation at 200° C. for 15 minutes. After cooling, the volatiles were removed under reduced pressure and residue purified via reversed-phase HPLC using an acetonitrile/water gradient (0.1% TFA). Fractions containing pure product were combined and lyophilized to provide (Compound 1, 50 mg, 15% yield) as an off-white powder: LCMS (M+H) 336.

Workup

  1. addition2.35 mmol) were added
  2. temperatureAfter cooling
  3. customthe volatiles were removed under reduced pressure and residue
  4. custompurified via reversed-phase
  5. additionFractions containing pure product

Sources & evidence

ORD record
ord-47234d8da79a41b6b6f425fe0a3500f7
Source dataset
uspto-grants-2012_09
Patent number
US08268999B2

Reaction notes

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