3H-spiro(isobenzofuran-1,4'-piperidin)-3-one → HCID 178519034, compound

HRID 413252Notes

Reaction equation

HRID 413252 reaction equation
Cl[C:2]1[NH:16][C:5]2=[N:6][CH:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:9]=[C:4]2[N:3]=1.[NH:17]1[CH2:22][CH2:21][C:20]2([C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:31])[O:23]2)[CH2:19][CH2:18]1>CC(N(C)C)=O>[C:10]1([C:8]2[N:9]=[C:4]3[N:3]=[C:2]([N:17]4[CH2:22][CH2:21][C:20]5([C:30]6[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=6)[C:24](=[O:31])[O:23]5)[CH2:19][CH2:18]4)[NH:16][C:5]3=[N:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 178478321HCID 178478321, compound

Product 1

HCID 178519034HCID 178519034, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Stir 2-chloro-5-phenyl-1H-imidazo[4,5-b]pyrazine (231 mg, 1 mmol) and spiro[isobenzofuran-1,4′-piperidin]-3-one (406 mg, 2 mmol) in dimethylacetamide (5 mL) at 120° C. for 14 hours. Cool the mixture and partition between EtOAc and half-saturated NaHCO3, wash several times with water, dry and concentrate in vacuo. Purify by chromatography (1:1 hexanes/EtOAc) to obtain 1′-(5-Phenyl-1H-imidazo[4,5-b]pyrazin-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one as a tan solid.

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 by chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-1fdd72d0eae642e9987afd1d02e84210
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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