Potassium Carbonate → 5-(4-Fluoro-phenyl)-pyrazine-2-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide

HRID 1174964Notes

Reaction equation

HRID 1174964 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][N:5]([CH3:25])[C:6]1[S:7][C:8]2[CH:14]=[C:13]([NH:15][C:16]([C:18]3[CH:23]=[N:22][C:21](Cl)=[CH:20][N:19]=3)=[O:17])[CH:12]=[CH:11][C:9]=2[N:10]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].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.O>[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][N:5]([CH3:25])[C:6]1[S:7][C:8]2[CH:14]=[C:13]([NH:15][C:16]([C:18]3[CH:23]=[N:22][C:21]([C:31]4[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=4)=[CH:20][N:19]=3)=[O:17])[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2856454-Fluorophenylboronic acidHCID 577717265-Chloro-pyrazine-2-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide

Product 1

HCID 577717355-(4-Fluoro-phenyl)-pyrazine-2-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amideYield 25%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Place 5-chloro-pyrazine-2-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide (73 mg, 0.187 mmol), Pd(PPh3)4 (29 mg, 0.025 mmol), 4-fluorophenyl boronic acid (27 mg, 0.193 mmol), and potassium carbonate (134 mg, 0.97 mmol) in a solution of 1,4-dioxane (5 mL) and water (1 mL): Heat the reaction to reflux overnight. Chromatograph (silica gel, eluting with 7-17% MeOH:DCM) to yield 21 mg (25%) of the title compound. mass spectrum (ion-spray): (m/z)=503.0 (M+1). Retention time=4.51 min.

Workup

  1. customthe reaction
  2. temperatureto reflux overnight
  3. washChromatograph (silica gel, eluting with 7-17% MeOH:DCM)

Sources & evidence

ORD record
ord-232a5755994a4215a3a5296a940eb6fe
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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