Pyridine → HCID 66746736, compound

HRID 1467281Notes

Reaction equation

HRID 1467281 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[C:15]=1[C:21]#[N:22])(=O)C.[S:23](Cl)(=[O:26])(=[O:25])N.[N:28]1C=CC=CC=1.[OH-].[Na+]>CC(N(C)C)=O>[NH2:28][C:21]1[C:15]2[C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])=[CH:19][CH:18]=[CH:17][C:16]=2[NH:20][S:23](=[O:26])(=[O:25])[N:22]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 24499Chlorosulfamic acidHCID 66746435HCID 66746435, compound

Product 1

HCID 66746736HCID 66746736, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 8-(3-amino-2-cyanophenoxy)octyl acetate (746 μmol, 227 mg) in DMA (3 mL) was added sulfamoyl chloride (1.492 mmol, 172 mg) and pyridine (4.476 mmol, 362 L). The reaction mixture was stirred at room temperature until completion, then quenched with sat. NaHCO3 (15 mL) and solid NaCl added. The precipate was collected and washed with water. The wet precipitate was suspended in EtOH (15 mL) and treated with NaOH (8.952 mmol, 1N, 8.95 mL). The reaction mixture was refluxed until completion then cooled to room temperature. Most of the EtOH and water were removed in vacuo, then the reaction mixture was dissolved in water (15 mL), extracted with ether (3×5 mL), filtered through a 0.45 μm PTFE frit, then acidified with 10% citric acid/water solution to pH 4-5. The precipitate was filtered off, washed with water and dried to give the desired product 146 mg (57.3%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) 1.265 (m, 6H), 1.380 (m, 4H), 1.785 (pentet, J=7 Hz, 2H), 3.348 (q, J=6 Hz, 2H), 4.303 (t, J=5 Hz, 2H), 6.580 (d, J=8 Hz, 1H), 6.724 (d, J=8 Hz, 1H), 7.428 (t, J=8 Hz, 1H), 7.796 (br. s, 1H), 8.329 (br. s, 1H), 10.922 (s, 1H). MS 342 (MH+).

Workup

  1. customquenched with sat. NaHCO3 (15 mL) and solid NaCl
  2. additionadded
  3. customThe precipate was collected
  4. washwashed with water
  5. temperatureThe reaction mixture was refluxed until completion
  6. temperaturethen cooled to room temperature
  7. customMost of the EtOH and water were removed in vacuo
  8. dissolutionthe reaction mixture was dissolved in water (15 mL)
  9. extractionextracted with ether (3×5 mL)
  10. filtrationfiltered through a 0.45 μm PTFE frit
  11. filtrationThe precipitate was filtered off
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-0e45496887994b40aa3cf663f21bef46
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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