Ammonia → HCID 76567875, compound

HRID 1728054Notes

Reaction equation

HRID 1728054 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:8]=[C:7]2[NH:9][C:10](=[O:32])[C:11]3([CH:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=4)[CH2:15][C:14](=[O:24])[N:13]([CH2:25][C:26](F)=[O:27])[CH:12]3[C:29]([CH3:31])=[CH2:30])[C:6]2=[CH:5][CH:4]=1>CO>[NH2:1][C:26]([CH2:25][N:13]1[C:14](=[O:24])[CH2:15][CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:11]2([C:6]3[C:7](=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=3)[NH:9][C:10]2=[O:32])[CH:12]1[C:29]([CH3:31])=[CH2:30])=[O:27]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 76567998HCID 76567998, compound

Product 1

HCID 76567875HCID 76567875, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ammonia (2 M, 10 mL) in methanol was added racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-fluorocarbonylmethyl-2′-isopropenylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.18 g, 0.39 mmol) prepared in example 116d. The reaction mixture was stirred at room temperature for overnight. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was separated, combined and concentrated. The residue was purified with chromatography (MeOH:EtOAc=5:95) to give racemic (2′R,3R,4′S)-1′-(aminocarbonyl-methyl)-6-chloro-4′-(3-chlorophenyl)-2′-isopropenylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield: 70 mg, 38.9%).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customThe residue was purified with chromatography (MeOH:EtOAc=5:95)

Sources & evidence

ORD record
ord-48f93a4224214a5b85fff1483b102ba4
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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