Water → HCID 22396212, compound

HRID 1070494Notes

Reaction equation

HRID 1070494 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([CH2:12][CH2:13][C:14]([OH:16])=O)[O:9][N:8]=1.Cl.[NH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.C(N(CC)CC)C.O>ClCCl.[Cl-].[Na+].O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([CH2:12][CH2:13][C:14]([NH:18][CH:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]2)=[O:16])[O:9][N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2756033tert-Butyl 4-aminopiperidine-1-carboxylate--hydrogen chloride (1/1)HCID 31643283-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)propanoic acid

Product 1

HCID 22396212HCID 22396212, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

3-[3-(2-Pyridinyl)-1,2,4-oxadiazol-5-yl]propanoic acid (0.60 g) was dissolved in dichloromethane (10 ml). 1,1-Carbonyldiimidazole (0.33 g) was added followed by tert-butyl 4-amino-1-piperidinecarboxylate hydrochloride (0.5 g) and triethylamine (0.31 ml). After 2 hours water, brine and dichloromethane were added and the phases separated. The organic phase was dried, filtered and evaporated and the residue was purified by chromatography eluting with ethyl acetate:methanol (33:1) to give the subtitle compound (0.40 g).

Workup

  1. customthe phases separated
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue was purified by chromatography
  6. washeluting with ethyl acetate:methanol (33:1)

Sources & evidence

ORD record
ord-c630edc8876343cd9980609724eae112
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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