2-Amino-5-methylpyridine → HCID 69539502, compound

HRID 1267724Notes

Reaction equation

HRID 1267724 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:22])[C@:15]([OH:21])([CH3:20])[C:16]([F:19])([F:18])[F:17].[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=1>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([S:9]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:22])[C@:15]([OH:21])([CH3:20])[C:16]([F:19])([F:18])[F:17]

Participants

4

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 86758935HCID 86758935, compound

Product 1

HCID 69539502HCID 69539502, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (R)-N-(2,3-dichloro-4-chlorosulphonylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (200 mg, 0.5 mmol) (Method 1) and 2-amino-5-methylpyridine (81 mg, 0.80 mmol) in pyridine (5 ml) was stirred at 80° C. overnight. The mixture was cooled to ambient temperature, poured onto water (50 ml) and extracted with EtOAc (2×25 ml). The organic layer was separated, washed with 1 M aqueous hydrochloric acid, saturated sodium hydrogen carbonate solution, brine, dried and evaporated to give the title compound as a solid (40 mg, 0.08 mmol); NMR: 1.6 (s, 3H), 2.1 (s, 3H), 7.1 (d, 1H), 7.6 (d, 1H), 7.75 (s, 1H), 8.1 (s, 2H); m/z 470.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. additionpoured onto water (50 ml)
  3. extractionextracted with EtOAc (2×25 ml)
  4. customThe organic layer was separated
  5. washwashed with 1 M aqueous hydrochloric acid, saturated sodium hydrogen carbonate solution, brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-86db82e5db1f473dbbfc2ef38443447b
Source dataset
uspto-grants-2003_04
Patent number
US06552225B1

Reaction notes

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