Ammonia → HCID 59025487, compound

HRID 1444832Notes

Reaction equation

HRID 1444832 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[CH:12]([C:23]#[N:24])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=1[O:21][CH3:22].[BH4-].[Na+].Cl.N>CO.O.O.O.O.O.O.[Co](Cl)Cl>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[CH2:4][C:3](=[O:2])[NH:24][CH2:23][CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=3[O:21][CH3:22])[C:6]=2[CH:7]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59025469HCID 59025469, compound

Product 1

HCID 59025487HCID 59025487, compound

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

118 mg of the compound from Example 27A (0.33 mol) are dissolved in 2.3 ml of methanol, and 156 mg of cobalt(II) chloride hexahydrate (0.66 mol) are added. While stirring at 0° C., 133 mg of sodium borohydride (3.51 mol) are added in portions over the course of 10 min. The reaction mixture is stirred at 0° C. for 30 min and at room temperature for 1 h. For working up, 7 ml of 1 N hydrochloric acid are added, and the mixture is stirred until a homogeneous solution results. The solution is made basic with concentrated ammonia solution and extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated in a rotary evaporator. The residue is dissolved in 10 ml of toluene and heated under reflux for 16 h. The solvent is removed in a rotary evaporator, and the residue is purified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80→95:5). 42 mg (40% of theory) of the title compound are obtained.

Workup

  1. stirringThe reaction mixture is stirred at 0° C. for 30 min and at room temperature for 1 h
  2. stirringthe mixture is stirred until a homogeneous solution
  3. customresults
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated in a rotary evaporator
  7. dissolutionThe residue is dissolved in 10 ml of toluene
  8. temperatureheated
  9. temperatureunder reflux for 16 h
  10. customThe solvent is removed in a rotary evaporator
  11. customthe residue is purified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-815114c324a845249d12ea9a04751ea9
Source dataset
uspto-grants-2010_02
Patent number
US07662956B2

Reaction notes

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