Hydrochloric Acid → HCID 67351596, compound

HRID 1672835Notes

Reaction equation

HRID 1672835 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]#[N:18])=[CH:14][CH:15]=2)[C:10]([N:19]2[CH2:28][C@H:27]3[N:23]([CH2:24][CH2:25][CH2:26]3)[C:22]3[N:29]=[C:30]([NH:33][CH2:34][CH3:35])[N:31]=[CH:32][C:21]=3[C:20]2=[O:36])=[CH:9]1)=O)(C)(C)C.[OH-].[Na+].Cl>C(O)C>[C:17]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH:9]=[C:10]2[N:19]1[CH2:28][C@H:27]2[N:23]([CH2:24][CH2:25][CH2:26]2)[C:22]2[N:29]=[C:30]([NH:33][CH2:34][CH3:35])[N:31]=[CH:32][C:21]=2[C:20]1=[O:36])#[N:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67348867HCID 67348867, compound

Product 1

HCID 67351596HCID 67351596, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-5-(1-Tert-butoxycarbonyl-5-cyanoindole-3-yl)-9-ethylamino-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (25.0 mg, 0.0513 mmol) obtained in Step 4 was dissolved in ethanol (2 mL), and the mixture was stirred at room temperature for 30 minutes after adding a 2 mol/L aqueous sodium hydroxide solution (0.256 mL, 0.513 mmol). The mixture was neutralized with 1 mol/L hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was then purified by preparative TLC to give the title compound (Compound 140) (19.2 mg, 96%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was then purified by preparative TLC

Sources & evidence

ORD record
ord-420afae00af14d5e8abfee4cdeca88ed
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

Loading…