Water → HCID 131728442, compound

HRID 1927460Notes

Reaction equation

HRID 1927460 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-baf3a4b0fd3d454eac1e485489f84a2d
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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