Pyridine → N-{3-Chloro-4-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]phenyl}propane-2-sulfonamide

HRID 2414325Notes

Reaction equation

HRID 2414325 reaction equation
[CH:1]([S:4](Cl)(=[O:6])=[O:5])([CH3:3])[CH3:2].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[CH2:24][O:23][C:22]3=[O:31])[CH2:17][CH2:16]2)=[C:11]([Cl:32])[CH:10]=1.N1C=CC=CC=1>C(#N)C>[Cl:32][C:11]1[CH:10]=[C:9]([NH:8][S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])[CH:14]=[CH:13][C:12]=1[N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][O:23][C:22]2=[O:31])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 824082-Propanesulfonyl chlorideHCID 226446801-[1-(4-Amino-2-chlorophenyl)piperidin-4-yl]-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 22644580N-{3-Chloro-4-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]phenyl}propane-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Isopropylsulphonyl chloride (0.03 ml) was added to a stirred solution of the product from example 120 step (ii) (0.05 g), pyridine (0.1 ml) in acetonitrile (0.9 ml) at room temperature. The mixture was stirred overnight, partitioned between ethyl acetate and water, the organics separated, washed with water, dried, and evaporated under reduced pressure. Purification was by chromatography eluting with 40% ethyl acetate/isohexane. Yield 0.015 g.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washthe organics separated, washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 40% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-558892f7f8eb43d7a45a1efaf662520b
Source dataset
uspto-grants-2004_11
Patent number
US06812226B2

Reaction notes

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