Sodium hydride → HCID 74928715, compound

HRID 504450Notes

Reaction equation

HRID 504450 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][C:34]([C:37](O)=[O:38])([CH3:36])[CH3:35])=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:52][S:53]([NH2:56])(=[O:55])=[O:54].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][C:34]([CH3:36])([CH3:35])[C:37]([NH:56][S:53]([CH3:52])(=[O:55])=[O:54])=[O:38])=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 76568060HCID 76568060, compound

Product 1

HCID 74928715HCID 74928715, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of racemic (2′S,3S,4′R)-4′-[5-bromo-2-(1-hydroxycarbonyl-1-methyl-ethoxy)-phenyl]-6-chloro-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (20 mg, 0.032 mmol) and CDI (11 mg, 0.064 mmol) in DMF (0.2 mL) was heated at 60° C. for 30 min, then cooled to room temperature. To this solution was added a mixture of methanesulfonamide (19 mg, 0.2 mmol) and NaH (8 mg, 60%, 0.2 mmol) in DMF (0.2 mL). The resulting mixture was stirred at room temperature for 10 min, purified by prep-HPLC to give the title compound as a white solid (10 mg).

Workup

  1. additionTo this solution was added
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-cedc1bb8594c49c5ac51ff83eeb9f03c
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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