Pyridine → HCID 59135593, compound

HRID 1960409Notes

Reaction equation

HRID 1960409 reaction equation
[C:1]([O:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([NH2:17])[CH:16]=1)[NH:13][C:12]([C:18]1[S:19][CH:20]([CH:23]([O:26][CH3:27])[O:24][CH3:25])[CH2:21][N:22]=1)=[CH:11]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34](Cl)(=[O:36])=[O:35].N1C=CC=C[CH:39]=1>C(OCC)(=O)C.C(OCC)C>[C:1]([O:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([N:17]([CH3:39])[S:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=3)(=[O:36])=[O:35])[CH:16]=1)[NH:13][C:12]([C:18]1[S:19][CH:20]([CH:23]([O:24][CH3:25])[O:26][CH3:27])[CH2:21][N:22]=1)=[CH:11]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 3787675Pyridine-2-sulfonyl ChlorideHCID 575032127-amino-2-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-5-yl pivalate

Product 1

HCID 59135593HCID 59135593, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-amino-2-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-5-yl pivalate (2.55 g) in pyridine (50 mL) was added dropwise a pyridine solution (10 mL) of pyridine-2-sulfonyl chloride (1.27 g) under ice-cooling, and the mixture was stirred at room temperature for 30 min. The reaction solution was diluted with ethyl acetate and diethyl ether, washed with water and saturated brine, dried (MgSO4), and concentrated. The residue was dissolved in N,N-dimethylformamide (50 mL), and potassium carbonate (1.1 g) and methyl iodide (0.45 mL) were added under ice-cooling. The mixture was stirred at room temperature for 30 min, diluted with ethyl acetate, washed with water and saturated brine, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=95:5-4:6) to give the title compound (3.1 g, yield 87%) as a pale-yellow amorphous powder.

Workup

  1. temperaturecooling
  2. washwashed with water and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in N,N-dimethylformamide (50 mL)
  6. additionpotassium carbonate (1.1 g) and methyl iodide (0.45 mL) were added under ice-
  7. temperaturecooling
  8. stirringThe mixture was stirred at room temperature for 30 min
  9. additiondiluted with ethyl acetate
  10. washwashed with water and saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=95:5-4:6)

Sources & evidence

ORD record
ord-53d2827034fc4ac999194a2dcb5c6b77
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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