Potassium Carbonate → HCID 57785847, compound

HRID 1399103Notes

Reaction equation

HRID 1399103 reaction equation
CS(Cl)(=O)=O.[Cl:6][C:7]1[C:15]2[N:14]=[C:13]([NH:16][C:17]3[C:18]([CH2:26][CH3:27])=[N:19][C:20]([CH3:25])=[N:21][C:22]=3[CH2:23][CH3:24])[N:12]([CH2:28][CH2:29][CH2:30]O)[C:11]=2[C:10]([C:32]([O:34][CH3:35])=[O:33])=[CH:9][CH:8]=1.S([O-])(=O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O.O.C(N(CC)CC)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:32]([O:34][CH3:35])=[O:33])=[C:11]2[C:15]=1[N:14]=[C:13]1[N:16]([C:17]3[C:22]([CH2:23][CH3:24])=[N:21][C:20]([CH3:25])=[N:19][C:18]=3[CH2:26][CH3:27])[CH2:30][CH2:29][CH2:28][N:12]21

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 68763068HCID 68763068, compound

Product 1

HCID 57785847HCID 57785847, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (1.10 mL, 13.4 mmol) was added to a stirred solution of methyl 4-chloro-2-[(4,6-diethyl-2-methylpyrimidin-5-yl)amino]-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylate (Reference example 125, 2.90 g, 6.71 mmol) and triethylamine (2.8 mL) in tetrahydrofuran (35 mL) at 0° C. The mixture was stirred at 0° C. for 90 min, and concentrated in vacuo. A mixture of the resulting mesylate and potassium carbonate (2.78 g, 20.1 mmol) in N,N-dimethylformamide (30 mL) was stirred at 70° C. for 4 hr. The mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 70-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (2.21 g, 5.34 mmol, 80% in 2 steps).

Workup

  1. concentrationconcentrated in vacuo
  2. stirringwas stirred at 70° C. for 4 hr
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel eluting with a 70-100% ethyl acetate/n-hexane gradient mixture
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a13145f8ff564230903ac0dc27f5879b
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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