Isopropyl Acetate → (6-Chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone

HRID 404547Notes

Reaction equation

HRID 404547 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.C(OC(C)=O)(C)C.[OH-].[Na+]>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7915Isopropyl AcetateHCID 14798Sodium HydroxideHCID 86661641(6-chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone L-tartaric acid

Product 1

HCID 58076653(6-Chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone

Procedure

A mixture of (6-chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone-L-tartaric acid (172 g, 386.9 mmol), iPrOAc (1.5 L), and 1 N NaOH(aq) (1.5 L) was thoroughly mixed and the resulting layers were separated. The aqueous layer was extracted with additional iPrOAc (1.5 L) and the combined organic layers were dried over magnesium sulfate. After filtration and concentration, (6-chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepam-1-yl)-methanone was obtained as a yellow oil.

Workup

  1. additionwas thoroughly mixed
  2. customthe resulting layers were separated
  3. extractionThe aqueous layer was extracted with additional iPrOAc (1.5 L)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. filtrationAfter filtration and concentration
  6. custom(6-chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepam-1-yl)-methanone was obtained as a yellow oil

Sources & evidence

ORD record
ord-f2618380e71d4719ae59d15897339bce
Source dataset
uspto-grants-2014_06
Patent number
US08748596B2

Reaction notes

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