Sodium Thiosulfate → HCID 57526818, compound

HRID 1452642Notes

Reaction equation

HRID 1452642 reaction equation
[C:1]([O:5][C:6]([N:8]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH3:42])=[CH:36][CH:35]=1)[C:9]1[N:20]2[C:16](=[CH:17][CH:18]=[N:19]2)[N:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][N:13]2[C@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:43]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[Cl:43][C:17]1[CH:18]=[N:19][N:20]2[C:16]=1[N:15]=[C:14]1[C:10]([CH2:11][CH2:12][N:13]1[C@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1)=[C:9]2[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:34]1[CH:35]=[CH:36][C:37]([O:40][CH2:41][CH3:42])=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 57526792HCID 57526792, compound

Product 1

HCID 57526818HCID 57526818, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution (2.0 mL) of tert-butyl (S)-3-{8-[tert-butoxycarbonyl-(4-ethoxyphenyl)amino]-6,7-dihydro-1,4,5,8a-tetraaza-s-indacen-5-yl}piperidine-1-carboxylate (12.5 mg, 0.0216 mmol), N-chlorosuccinimide (15.3 mg, 0.114 mmol) was added at room temperature and the mixture was stirred at room temperature for 1 hr. After the reaction, aqueous sodium thiosulfate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was evaporated to obtain the title compound.

Workup

  1. additionwas added to the reaction solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialbrine and dried over sodium sulfate
  5. filtrationAfter the sodium sulfate was filtered off
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d9dc1de5f9584fd8b905164903035b55
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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