Water → HCID 131728442, compound

HRID 1172472Notes

Reaction equation

HRID 1172472 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[Cl:9][C:10]1[C:15]2[O:16][C:17]3[C:26]([CH3:27])=[CH:25][C:24]([C:28]([OH:30])=[O:29])=[CH:23][C:18]=3[S:19](=[O:22])(=[O:21])[CH2:20][C:14]=2[CH:13]=[C:12]([S:31](Cl)(=[O:33])=[O:32])[CH:11]=1.O>C(OCC)(=O)C>[Cl:9][C:10]1[C:15]2[O:16][C:17]3[C:26]([CH3:27])=[CH:25][C:24]([C:28]([OH:30])=[O:29])=[CH:23][C:18]=3[S:19](=[O:22])(=[O:21])[CH2:20][C:14]=2[CH:13]=[C:12]([S:31](=[O:32])(=[O:33])[NH:1][CH2:2][C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 310183-PyridinemethanamineHCID 131728441HCID 131728441, compound

Product 1

HCID 131728442HCID 131728442, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(Aminomethyl)pyridine (0.22 mL, 2.1 mmol) was added to a suspension of Example 49j (0.8 g, 1.8 mmol) in ethyl acetate (40 mL). The reaction mixture was stirred at room temperature for 15 h, treated with water and extracted with butanol. The organic layer was washed with water, dried, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound. Yield: 0.2 g, (20%); 1H NMR (DMSO-d6): δ 2.69 (s, 3H, CH3), 4.18 (d, 2H, CH2), 5.45 (s, 2H, CH2), 7.26 (d, 1H, Ar), 7.6 (d, 1H, Ar), 7.9 (s, 1H, Ar), 8.09 (s, 1H, Ar), 8.18 (s, 1H, Ar), 8.24 (s, 1H, Ar), 8.41 (d, 1H, Ar), 8.47 (s, 1H, Ar), 8.6 (s, 1H, OH).

Workup

  1. extractionextracted with butanol
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-a19b26fd1675438a9117505debae5e20
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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