Sulfuric Acid → HCID 89545048, compound

HRID 2283438Notes

Reaction equation

HRID 2283438 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[C:11]([F:28])=[C:12]([C@H:17]([NH:20][CH:21]([CH:25]([CH3:27])[CH3:26])[CH2:22][C:23]#[N:24])[CH2:18][CH3:19])[CH:13]=[CH:14][C:15]=2[Cl:16])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:30].C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[C:11]([F:28])=[C:12]([C@H:17]([NH:20][C@@H:21]([CH:25]([CH3:27])[CH3:26])[CH2:22][C:23]([NH2:24])=[O:30])[CH2:18][CH3:19])[CH:13]=[CH:14][C:15]=2[Cl:16])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 89544704HCID 89544704, compound

Product 1

HCID 89545048HCID 89545048, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Step 2 To a rapidly stirred solution of crude 3-{[(1R)-1-{3-[(6-aminopyridin-3-yl)carbonyl]-4-chloro-2-fluorophenyl}propyl]amino}-4-methylpentanenitrile (0.911 mmol) in toluene (2.91 mL) and water (0.145 mL) at 0° C. was added sulfuric acid (0.966 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was made neutral by the addition of saturated Na2CO3 solution followed by saturated NaHCO3 solution and was extracted into EtOAc (×2). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by chiral preparative HPLC to give (3R)-3-{[(1R)-1-{3-[(6-aminopyridin-3-yl)carbonyl]-4-chloro-2-fluorophenyl}propyl]amino}-4-methylpentanamide which was converted to the HCl salt, 0.0656 g and (3S)-3-{[(1R)-1-{3-[(6-aminopyridin-3-yl)carbonyl]-4-chloro-2-fluorophenyl}propyl]-amino}-4-methylpentanamide which was also converted to the HCl salt, 0.0259 g.

Workup

  1. extractionwas extracted into EtOAc (×2)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chiral preparative HPLC

Sources & evidence

ORD record
ord-f79b12546c5d41cebe4c2ba0660d2076
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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