2-Amino-3-methylpyridine → Susalimod

HRID 1653920Notes

Reaction equation

HRID 1653920 reaction equation
[CH3:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C([O:12][C:13]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:20][C:14]=1[C:15]([O:17]CC)=[O:16])(=O)C>N1C=CC=CC=1>[OH:12][C:13]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([NH:8][C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:20][C:14]=1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 19423378HCID 19423378, compound

Product 1

HCID 3086668Susalimod

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-methyl-2-pyridinamine (1.3 g, 12 mmol) was dissolved in dry pyridine (20 ml) and ethyl 2-acetyloxy-5-[(4-chlorosulfonylphenyl)ethynyl]-benzoate (4.1 g, 10 mmol) was added. The solution was kept at ambient temperature for 18 h. The solvent was evaporated and the residue dissolved in a small amount of tetrahydrofuran. The solution was added to a refluxing solution of potassium hydroxide (6 g) in water 100 ml) and ethanol (50 ml). After 15 min the solution was acidified with formic acid to produce a precipitate. The solid was collected by filtration, washed with water and dried. Yield 1.2 g, 29%.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in a small amount of tetrahydrofuran
  3. additionThe solution was added to a refluxing solution of potassium hydroxide (6 g) in water 100 ml) and ethanol (50 ml)
  4. waitAfter 15 min the solution was acidified with formic acid
  5. customto produce a precipitate
  6. filtrationThe solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-ec277c30de07475aaf19dba2d1e99ac1
Source dataset
uspto-grants-1995_04
Patent number
US05403930

Reaction notes

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