Pyridine → HCID 69539604, compound

HRID 1267723Notes

Reaction equation

HRID 1267723 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.N1C=CC=CC=1.[Cl:16][C:17]1[C:22]([Cl:23])=[C:21]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:19][C:18]=1[NH:28][C:29](=[O:37])[C@:30]([OH:36])([CH3:35])[C:31]([F:34])([F:33])[F:32]>CN(C)C1C=CN=CC=1.CCOC(C)=O>[Cl:16][C:17]1[C:22]([Cl:23])=[C:21]([S:24]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:26])=[O:25])[CH:20]=[CH:19][C:18]=1[NH:28][C:29](=[O:37])[C@:30]([OH:36])([CH3:35])[C:31]([F:32])([F:33])[F:34]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7732P-AnisidineHCID 86758935HCID 86758935, compound

Product 1

HCID 69539604HCID 69539604, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of p-anisidine (74 mg, 0.6 mmol), pyridine (0.14 ml, 1.0 mmol) and 4-dimethylaminopyridine (10 mg) in EtOAc (10 ml) was added a solution of (R)-N-[2,3-dichloro-4-(chlorosulphonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (200 mg, 0.5 mmol) (Method 1) in EtOAc (10 ml). The resultant mixture was stirred at ambient temperature overnight, washed with 1 M aqueous hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue was chromatographed on a Bond Elut column (using 10% EtOAc in DCM as eluent) to give the title compound as a foam (114 mg, 0.23 mmol); NMR: 1.6 (s, 3H), 3.6 (s, 3H), 6.8 (d, 2H), 7.0 (d, 2H), 7.95 (d, 1H), 8.1 (d, 1H); m/z 485.

Workup

  1. washwashed with 1 M aqueous hydrochloric acid, saturated sodium hydrogen carbonate solution and brine
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on a Bond Elut column (using 10% EtOAc in DCM as eluent)

Sources & evidence

ORD record
ord-e917c31eede943e9a1186c33fccfa081
Source dataset
uspto-grants-2003_04
Patent number
US06552225B1

Reaction notes

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