Hydrochloric Acid → HCID 58487569, compound

HRID 1477498Notes

Reaction equation

HRID 1477498 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)[O:4][N:3]=1.Cl.CC(OC)(C)C>C(O)C>[NH2:1][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[O:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 58487573HCID 58487573, compound

Product 1

HCID 58487569HCID 58487569, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
40 °C

Procedure

tert-Butyl 3-(3-amino-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate 26 (0.33 g, 0.00123 mol) was dissolved in 2 mL ethanol. Hydrochloric acid in ethanol (2.5 M) (2.00 mL, 0.00493 mol) was added and the mixture was heated to 40° C. for 1 hour. 12 mL of MTBE was added and the product precipitated from solution. The solids were filtered and washed with 2×5 mL MTBE, and recrystallized 3 times from methanol:isopropanol to give 127 mg white solid. MS (ESI) m/z 168 [M+1]+. 1H NMR (DMSO-d6) δ 1.67-1.82 (m, 3 H), 2.08-2.12 (d, 1 H), 2.86-2.90 (t, 1 H), 3.06-3.12 (t, 1 H), 3.21-3.24 (d, 1 H), 3.33 (s, 2H), 3.49-3.52 (d, 1 H), 6.32 (s, 2H).

Workup

  1. customthe product precipitated from solution
  2. filtrationThe solids were filtered
  3. washwashed with 2×5 mL MTBE
  4. customrecrystallized 3 times from methanol

Sources & evidence

ORD record
ord-83a0e013b3444545a565f81761af095c
Source dataset
uspto-grants-2016_08
Patent number
US09403806B1

Reaction notes

Loading…