Pyridine → HCID 68505538, compound

HRID 750556Notes

Reaction equation

HRID 750556 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:3]=1[C:13]([NH2:15])=[O:14].N1C=CC=CC=1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24]>O1CCCC1>[C:26]1([O:25][C:23](=[O:24])[NH:1][C:2]2[S:6][N:5]=[C:4]([S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:3]=2[C:13](=[O:14])[NH2:15])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 15891Phenyl chloroformate2×HCID 53923417HCID 53923417, compound

Product 1

HCID 68505538HCID 68505538, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-3-pentylsulfanyl-isothiazole-4-carboxylic acid amide (2.2 g, 9.0 mmol) in 36 mL of tetrahydrofuran was added pyridine (0.90 g, 11 mmol) and phenyl chloroformate (1.7 g, 11 mmol). After stirring for 3 hours, additional pyridine (0.15 g, 1.9 mmol) and phenyl chloroformate (0.29 g, 1.9 mmol) was added, and the mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo, diluted with water and extracted 2× with CH2Cl2, 1× with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated for 12 hours with ether-hexane, and the resulting solids were collected and dried in vacuo, affording 2.6 g (79%) of (4-carbamoyl-3-pentylsulfanyl-isothiazol-5-yl)-carbamic acid phenyl ester as a colorless solid. 1H NMR (300 MHz, CDCl3) δ 7.41 (t, 2 H, J=7.3 Hz), 7.29-7.20 (m, 3H), 3.31 (t, 2H, J=7.3 Hz), 1.72 (m, 2H), 1.50-1.30 (m, 4H), 0.90 (t, 3H, J=7.1 Hz) ppm; MS (APCl, m/z): 366 [M+H]+.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted 2× with CH2Cl2, 1× with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated for 12 hours with ether-hexane
  10. customthe resulting solids were collected
  11. customdried in vacuo

Sources & evidence

ORD record
ord-113f41f0eae44a728786a3107669139f
Source dataset
uspto-grants-2008_07
Patent number
US07405218B2

Reaction notes

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