Hydrochloric Acid → HCID 67227970, compound

HRID 2044992Notes

Reaction equation

HRID 2044992 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:20][CH2:19][NH:18][C:17](=O)[CH:16]2[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:4][CH:3]=1.B.CSC.Cl.[NH4+].[OH-]>O1CCCC1.O1CCOCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH:16]2[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 67226198HCID 67226198, compound

Product 1

HCID 67227970HCID 67227970, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of EXAMPLE 27D in tetrahydrofuran (3.6 mL) was added borane-methyl sulfide complex (10M in tetrahydrofuran) (0.24 mL). The reaction was heated under reflux for 16 hours, then cooled in an ice/water bath. Methanol (5 mL) was added carefully, and the mixture was stirred cold for 75 minutes. Then 4N HCl in dioxane (0.65 mL) was added and the reaction heated under reflux for 60 minutes. After cooling to room temperature, 1N NH4OH (2.6 mL) was added and the reaction was stirred for 15 minutes. Then the reaction was concentrated, redissolved in methanol, concentrated, redissolved in toluene and concentrated. The crude solids were slurried in CHCl3/methanol, the solids were filtered off, and the filtrate concentrated to afford the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 16 hours
  3. temperaturecooled in an ice/water bath
  4. temperaturethe reaction heated
  5. temperatureunder reflux for 60 minutes
  6. stirringthe reaction was stirred for 15 minutes
  7. concentrationThen the reaction was concentrated
  8. dissolutionredissolved in methanol
  9. concentrationconcentrated
  10. dissolutionredissolved in toluene
  11. concentrationconcentrated
  12. filtrationthe solids were filtered off
  13. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-185b172ab0e0446fa875d7371e3d1f57
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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