3H-spiro(isobenzofuran-1,4'-piperidin)-3-one → HCID 178519033, compound

HRID 413246

Reaction equation

HRID 413246 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([S:11]([C:14]([F:17])([F:16])[F:15])(=[O:13])=[O:12])=[CH:10][C:4]=2[N:3]=1.[NH:18]1[CH2:23][CH2:22][C:21]2([C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25](=[O:32])[O:24]2)[CH2:20][CH2:19]1>CC(N(C)C)=O>[F:15][C:14]([F:17])([F:16])[S:11]([C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([N:18]3[CH2:23][CH2:22][C:21]4([C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:25](=[O:32])[O:24]4)[CH2:20][CH2:19]3)=[N:3][C:4]=2[CH:10]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 178527270HCID 178527270, compound

Product 1

HCID 178519033HCID 178519033, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Stir 2-chloro-5-trifluoromethylsulfonyl-1H-benzimidazole (185 mg) and spiro[isobenzofuran-1,4′-piperidin]-3-one (263 mg) in dimethylacetamide (6 mL) at 195° C. for 1 hour. Cool the mixture and partition between EtOAc and half-saturated NaHCO3, wash several times with water, dry and concentrate in vacuo. Purify the residue by chromatography (1:1 hexanes/EtOAc) to obtain 1′-(5-trifluoromethylsulfonyl-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one.

Workup

  1. temperatureCool the mixture
  2. custompartition between EtOAc and half-saturated NaHCO3
  3. washwash several times with water
  4. customdry
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-409f3a4d3f4148a19b872db543aaf871
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Linked notes

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