Sodium hydride → HCID 59428086, compound

HRID 504455Notes

Reaction equation

HRID 504455 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:38])[C@@:10]3([C@@H:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26])[CH2:14][C:13](=[O:29])[NH:12][C@H:11]3[C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=3[CH3:37])[C:5]2=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:51][S:52]([NH2:55])(=[O:54])=[O:53].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:38])[C@@:10]3([C@@H:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([CH3:28])([CH3:27])[C:25]([NH:55][S:52]([CH3:51])(=[O:54])=[O:53])=[O:26])[CH2:14][C:13](=[O:29])[NH:12][C@H:11]3[C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=3[CH3:37])[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 57565834HCID 57565834, compound

Product 1

HCID 59428086HCID 59428086, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of chiral (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(2-hydroxy-1,1-dimethyl-ethoxy)-phenyl]-2′-[5-fluoro-2-methylphenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (20 mg, 0.035 mmol) and CDI (11 mg, 0.068 mmol) in DMF (0.2 mL) was heated at 60° C. for 30 min, and then cooled to root 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 (7 mg).

Workup

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

Sources & evidence

ORD record
ord-2e134535f83d42c09cf702ea7bb5d4bf
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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