Hydrochloric Acid → 2-(2-Methoxypyridin-4-yl)-2,4-diazabicyclo[3.1.0]hexan-3-one

HRID 523582Notes

Reaction equation

HRID 523582 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:14]3[CH:12]([CH2:13]3)[N:11](C(OCC3C=CC=CC=3)=O)[C:10]2=[O:25])[CH:6]=[CH:5][N:4]=1.Cl>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[C:10](=[O:25])[NH:11][CH:12]3[CH:14]2[CH2:13]3)[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 70982767Benzyl 4-(2-methoxypyridin-4-yl)-3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate

Product 1

HCID 709820752-(2-Methoxypyridin-4-yl)-2,4-diazabicyclo[3.1.0]hexan-3-oneYield 67%

Procedure

Using analogous reagents and reaction conditions as described in Example 30 for the preparation of I-30c above, benzyl 4-(2-methoxypyridin-4-yl)-3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate (150.0 mg, 0.442 mmol) was treated with 10.0 mL of 6N HCl to yield the crude product. Purification by column chromatography on silica gel (1.5% methanol in chloroform) afforded 60 mg of the product (67% yield).

Workup

  1. customreagents and reaction conditions
  2. customto yield the crude product
  3. customPurification by column chromatography on silica gel (1.5% methanol in chloroform)

Sources & evidence

ORD record
ord-61d95f7f5f704109afbfd1fe0e9b4140
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

Loading…