Hydrogen Bromide → HCID 66732466, compound

HRID 1963501Notes

Reaction equation

HRID 1963501 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C@H:7]2[CH2:12][C@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][N:8]2C(OCC2C=CC=CC=2)=O)=[N:3]1.Br>>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C@H:7]2[CH2:12][C@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][NH:8]2)=[N:3]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730440HCID 131730440, compound

Product 1

HCID 66732466HCID 66732466, compound

Procedure

Trans-benzyl 2-(2-methyl-2H-tetrazol-5-yl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (99 mg, 0.26 mmol) (from example 81, step 3) was dissolved in hydrogen bromide (33% in HOAc, 1.35 mL, 7.73 mmol) and reacted for 1 h. The mixture was evaporated and the residue was partitioned between water and EtOAc. The aqueous phase was purified by preparative HPLC on a Kromasil C8 column (10 μm 250×50 ID mm) using a gradient of 0-15% Acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 20 minutes with a flow of 100 mL/min. 5-(Trans-2-(2-methyl-2H-tetrazol-5-yl)piperidin-4-yl)isoxazol-3(2H)-one (45 mg, 70%). 1H NMR (400 MHz, cd3od) δ 1.83-2.05 (m, 2H), 2.21-2.31 (m, 1H), 2.36-2.44 (m, 1H), 2.93-3.06 (m, 2H), 3.17-3.25 (m, 1H), 4.37 (s, 3H), 4.49 (t, 1H), 5.77 (s, 1H). HRMS Calcd for [C10H14N6O2+H]+: 251.1256. Found: 251.1262.

Workup

  1. customreacted for 1 h
  2. customThe mixture was evaporated
  3. customthe residue was partitioned between water and EtOAc
  4. customThe aqueous phase was purified by preparative HPLC on a Kromasil C8 column (10 μm 250×50 ID mm)
  5. custombuffer over 20 minutes

Sources & evidence

ORD record
ord-c7ed9305f09a40a1bc622d1c9ed11049
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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