Sodium Hydroxide → HCID 24986678, compound

HRID 1174551Notes

Reaction equation

HRID 1174551 reaction equation
C1(S([N:10]2[C:19]3[CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][NH:15][C:14](=[O:22])[C:13]=3[S:12][CH:11]2[C:23]2[CH:28]=[CH:27][N:26]=[C:25]3[NH:29][CH:30]=[CH:31][C:24]=23)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[CH3:20][C:17]1([CH3:21])[CH2:16][NH:15][C:14](=[O:22])[C:13]2[S:12][C:11]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]4[NH:29][CH:30]=[CH:31][C:24]=34)=[N:10][C:19]=2[CH2:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86635769HCID 86635769, compound

Product 1

HCID 24986678HCID 24986678, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Benzene sulfonyl-5,6,7,8-tetrahydro-7,7-dimethyl-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiazolo[5,4-c]azepin-4-one (Made using methods D and E) (79 mg, 1.0 Eq.) was suspended/dissolved in EtOH (4.5 mL) and NaOH (15 wt %, 0.5 mL, 11 Eq.) was added. The reaction mixture was refluxed for 4 hours. The reaction mixture was then allowed to cool to RT, and the solvent removed in vacuo. The mixture was partitioned between EtOAc/sat. aq. NH4Cl, and extracted into EtOAc (3×20 mL). The combined organic layers were washed with 15 wt % NaOH (1×10 mL), brine (1×10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification was achieved using column chromatography (5% MeOH/95% DCM), followed by tritration in Et2O. The precipitate was then washed with pentane. The title compound was obtained as a tangerine solid (27.8 mg, 52% yield); 1H NMR (DMSO D6) 1.1 (6H, s), 3.0 (4H, m), 7.0 (1H, m), 7.6 (1H, m), 7.7 (1H, m), 8.3 (2H, m), 12.1 (1H, br s); LC/MS M+1 (obs.) 313.20; LC/MS M−1 (obs.) 311.40.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customthe solvent removed in vacuo
  3. customThe mixture was partitioned between EtOAc/
  4. extractionaq. NH4Cl, and extracted into EtOAc (3×20 mL)
  5. washThe combined organic layers were washed with 15 wt % NaOH (1×10 mL), brine (1×10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification
  10. washThe precipitate was then washed with pentane

Sources & evidence

ORD record
ord-dc5ab27b2361409da11b3c57b61a06e0
Source dataset
uspto-grants-2010_11
Patent number
US07838517B2

Reaction notes

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