Pyridine → HCID 69539577, compound

HRID 1267727Notes

Reaction equation

HRID 1267727 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].N1C=CC=CC=1.[NH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[N:34][CH:35]=1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([S:9]([NH:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[N:34][CH:35]=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

5

Reactant 3

HCID 1049PyridineHCID 811216-Methoxy-3-pyridinylamineHCID 86758935HCID 86758935, compound

Product 1

HCID 69539577HCID 69539577, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (R)-N-(2,3-Dichloro-4-chlorosulphonylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (Method 1; 0.3 mmol) and pyridine (0.33 mmol) in DCM (5 ml) was added to a solution of 5-amino-2-methoxypyridine (0.3 mmol) in DCM (2 ml). The resultant mixture was stirred at ambient temperature overnight. The DCM was evaporated and resulting mixture was partitioned between EtOAc (5 ml) and 1 M HCl (4 ml), the EtOAc layer was separated and washed with saturated aqueous sodium hydrogen carbonate solution and brine then dried and evaporated to give the title compound as a gum (50 mg). M/z 486.

Workup

  1. customThe DCM was evaporated
  2. customresulting mixture
  3. customwas partitioned between EtOAc (5 ml) and 1 M HCl (4 ml)
  4. customthe EtOAc layer was separated
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution and brine
  6. customthen dried
  7. customevaporated

Sources & evidence

ORD record
ord-9d5e4d3fdd4645eea32cfe053cc18b3e
Source dataset
uspto-grants-2003_04
Patent number
US06552225B1

Reaction notes

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