Pyridine → HCID 131728440, compound

HRID 1927459Notes

Reaction equation

HRID 1927459 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:7]2[CH2:9][CH2:8]2)=[N:5][N:6]=1.[Cl:10][C:11]1[C:16]2[O:17][C:18]3[C:27]([CH3:28])=[CH:26][C:25]([C:29]([OH:31])=[O:30])=[CH:24][C:19]=3[S:20](=[O:23])(=[O:22])[CH2:21][C:15]=2[CH:14]=[C:13]([S:32](Cl)(=[O:34])=[O:33])[CH:12]=1.N1C=CC=CC=1>C(OCC)(=O)C>[Cl:10][C:11]1[C:16]2[O:17][C:18]3[C:27]([CH3:28])=[CH:26][C:25]([C:29]([OH:31])=[O:30])=[CH:24][C:19]=3[S:20](=[O:23])(=[O:22])[CH2:21][C:15]=2[CH:14]=[C:13]([S:32](=[O:33])(=[O:34])[NH:1][C:2]2[S:3][C:4]([CH:7]3[CH2:9][CH2:8]3)=[N:5][N:6]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7170215-Cyclopropyl-1,3,4-thiadiazol-2-amineHCID 131728441HCID 131728441, compound

Product 1

HCID 131728440HCID 131728440, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-cyclopropyl-1,3,4-thiadiazole (0.236 g, 0.126 mmol) was added to a mixture of Example 49j (0.3 g, 0.68 mmol) and pyridine (8 mL) in ethyl acetate (10 mL). The reaction mixture was stirred at room temperature for 15 h, concentrated, treated with water and extracted with n-butanol. The organic extract was washed with water, dried concentrated and purified using flash chromatography (silica gel, 4% methanol/chloroform) to obtain the title compound. Yield: 0.03 g, (8%); 1H NMR (DMSO-d6): δ 0.98 (m, 2H, CH2), 1.12 (d, 2H, CH2), 2.3 (m, 1H, CH), 2.7 (s, 3H, CH3), 5.46 (s, 2H, CH2), 7.95 (d, 1H, Ar,), 8.06 (s, 1H, Ar), 8.14 (s, 1H, Ar), 8.16 (s, 1H, Ar).

Workup

  1. concentrationconcentrated
  2. additiontreated with water
  3. extractionextracted with n-butanol
  4. extractionThe organic extract
  5. washwas washed with water
  6. customdried
  7. concentrationconcentrated
  8. custompurified

Sources & evidence

ORD record
ord-10cad257901d454bb570490f29f0643e
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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