Hydrochloric Acid → HCID 58248298, compound

HRID 388860Notes

Reaction equation

HRID 388860 reaction equation
[O:1]=[C:2]1[N:10](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:32][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([CH:30]=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2.Cl.OS(O)(=O)=O.[OH-].[Na+]>CO.O>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:32][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([CH:30]=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 58550623HCID 58550623, compound

Product 1

HCID 58248298HCID 58248298, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of (2S)-2′-oxo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,1′,2′,3-tetrahydrospiro[cyclopenta[b]quinoline-2,3′-pyrrolo[2,3-b]pyridine]-7-carbaldehyde from Step I (142 mg, 0.320 mmol) in MeOH (17 mL) was introduced gaseous anhydrous hydrogen chloride by bubbling the gas through the solution until the MeOH was saturated and mildly warmed. This saturation with HCl was repeated once again after 3 hours then the sealed reaction was allowed to sit at ambient temperature for 19 hours. The solution was then purged with a stream of nitrogen for 20-30 minutes, before being concentrated in vacuo. MeOH (50 mL) was added, then removed in vacuo, repeating this addition/concentration twice to remove excess HCl. The residue was dissolved in MeOH (17 mL) prior to the addition of concentrated aqueous NH4OH (0.7 mL). After 20 minutes the MeOH was removed in vacuo, fresh MeOH (50 mL) was added then remove in vacuo to produce a residue. This residue was dissolved in water (1.35 mL) plus 4 drops on cone. H2SO4. This aqueous solution was transferred to an Erlenmeyer flask using water (3 mL) and 2 more drops of conc. H2SO4. Slow neutralization with aqueous NaOH (1 M, ˜2.5 mL) provided a solid which was filtered, washed with water, air dried and vacuum dried to give the title compound. MS: m/z=316 (M+1).

Workup

  1. customby bubbling the gas through the solution until the MeOH
  2. temperaturemildly warmed
  3. customthe sealed reaction
  4. waitto sit at ambient temperature for 19 hours
  5. customThe solution was then purged with a stream of nitrogen for 20-30 minutes
  6. concentrationbefore being concentrated in vacuo
  7. additionMeOH (50 mL) was added
  8. customremoved in vacuo
  9. concentrationthis addition/concentration twice
  10. customto remove excess HCl
  11. dissolutionThe residue was dissolved in MeOH (17 mL)
  12. additionto the addition of concentrated aqueous NH4OH (0.7 mL)
  13. customAfter 20 minutes the MeOH was removed in vacuo, fresh MeOH (50 mL)
  14. additionwas added
  15. customthen remove in vacuo
  16. customto produce a residue
  17. customprovided a solid which
  18. filtrationwas filtered
  19. washwashed with water, air
  20. customdried
  21. customvacuum dried

Sources & evidence

ORD record
ord-f44a3adcacd349379965a8e271e5a167
Source dataset
uspto-grants-2013_02
Patent number
US08377955B2

Reaction notes

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