Potassium tert-butoxide → HCID 178477639, compound

HRID 1671653Notes

Reaction equation

HRID 1671653 reaction equation
[CH3:1][NH2:2].CO.[CH2:5]([S:7]([C:10]1[CH:37]=[CH:36][C:13]([O:14][C:15]2[C:16]([CH:30]([OH:35])[C:31](OC)=[O:32])=[CH:17][C:18]3[N:22]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[NH:20][C:19]=3[CH:29]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:6].C[C:39](C)([O-:41])C.[K+]>>[CH2:5]([S:7]([C:10]1[CH:11]=[CH:12][C:13]([O:14][C:15]2[C:16]([CH:30]3[O:35][C:39](=[O:41])[N:2]([CH3:1])[C:31]3=[O:32])=[CH:17][C:18]3[N:22]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[NH:20][C:19]=3[CH:29]=2)=[CH:36][CH:37]=1)(=[O:8])=[O:9])[CH3:6]

Participants

4

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 57454252Monomethylamine methanolHCID 178477645HCID 178477645, compound

Product 1

HCID 178477639HCID 178477639, compound

Conditions

Temperature
50 °C

Procedure

1 N methylamine/methanol solution (2 ml) was added to methyl (6-(4-(ethylsulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazol-5-yl)(hydroxy)acetate (14 mg) obtained in (step 2), and the reaction liquid was stirred at 50° C. for 3 hours. The solvent was evaporated away under reduced pressure, and to a tetrahydrofuran (2 ml) solution of the resulting residue, added were 1,1′-carbonyldiimidazole (2.5 mg) and triethylamine (0.01 ml), and the reaction liquid was stirred at 70° C. for 2 hours. then, potassium t-butoxide (3 mg) was added to it, and the reaction liquid was stirred at 70° C. for 5 minutes. The reaction mixture was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid), and the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline water in that order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound as a yellow solid.

Workup

  1. customobtained in (step 2)
  2. customthe reaction liquid
  3. customThe solvent was evaporated away under reduced pressure
  4. additionto a tetrahydrofuran (2 ml) solution of the resulting residue, added
  5. customthe reaction liquid
  6. stirringwas stirred at 70° C. for 2 hours
  7. customthe reaction liquid
  8. stirringwas stirred at 70° C. for 5 minutes
  9. customThe reaction mixture was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid)
  10. additionthe resulting fraction was diluted with ethyl acetate
  11. washwashed with aqueous saturated sodium bicarbonate and saturated saline water in that order
  12. dry with materialdried with anhydrous sodium sulfate
  13. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-cfb5e113289f482aac37d5410cc71e64
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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