Pyridine → HCID 131728440, compound

HRID 1172471Notes

Reaction equation

HRID 1172471 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-05d02f63da8a4a9c9163f3f7be4f5aa2
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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