Pyridine → HCID 88147945, compound

HRID 1602504Notes

Reaction equation

HRID 1602504 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([C:12]1[N:13]=[C:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:48]=[CH:49][CH:50]=2)[C:22]([NH:24][C:25]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][S:34]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:28]=[CH:27][C:26]=2[O:44][CH2:45][CH2:46][NH2:47])=[O:23])[S:15][CH:16]=1)([CH3:11])([CH3:10])[CH3:9].N1C=CC=CC=1>ClCCl>[OH2:3].[C:8]([C:12]1[N:13]=[C:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:48]=[CH:49][CH:50]=2)[C:22]([NH:24][C:25]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][S:34]([C:37]3[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=3)(=[O:35])=[O:36])[CH:28]=[CH:27][C:26]=2[O:44][CH2:45][CH2:46][NH:47][C:1](=[O:3])[CH3:2])=[O:23])[S:15][CH:16]=1)([CH3:11])([CH3:9])[CH3:10].[C:8]([C:12]1[N:13]=[C:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:48]=[CH:49][CH:50]=2)[C:22]([NH:24][C:25]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][S:34]([C:37]3[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=3)(=[O:35])=[O:36])[CH:28]=[CH:27][C:26]=2[O:44][CH2:45][CH2:46][NH:47][C:1](=[O:3])[CH3:2])=[O:23])[S:15][CH:16]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 19611365HCID 19611365, compound

Product 1

HCID 88147945HCID 88147945, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, acetic anhydride (30 μl, 0.3 mmol) was added to a mixture of 3-[(4-tert-butyl-2-thiazolyl)methoxy]-5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-(2-aminoethoxy)benzanilide 1.4 hydrochloride.0.7 hydrate (170 mg, 0.24 mmol), dichloromethane (2 ml) and pyridine (32 μl, 0.4 mmol), and the resulting mixture was stirred at room temperature for 3 hours. Ice-water was added to the reaction solution and the mixture was stirred for 1 hour. The product formed was extracted with chloroform and the resulting organic layer was washed with 20% potassium hydrogensulfate aqueous solution, saturated sodium bicarbonate aqueous solution and distilled water in that order, dried over anhydrous magnesium sulfate, and then concentrated. The resulting residue was crystallized from chloroform-ether to give 3-[(4-tert-butyl-2-thiazolyl)methoxy]-5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-(2-acetylaminoethoxy)benzanilide hemihydrate (97 mg, 0.14 mmol, 58%) as white crystals.

Workup

  1. temperatureUnder ice-cooling
  2. customThe product formed
  3. extractionwas extracted with chloroform
  4. washthe resulting organic layer was washed with 20% potassium hydrogensulfate aqueous solution, saturated sodium bicarbonate aqueous solution
  5. distillationdistilled water in that order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe resulting residue was crystallized from chloroform-ether

Sources & evidence

ORD record
ord-858d955fc9fa4e98bcb2db744b45b737
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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