Potassium Iodide → 2-chloro-N-isopropyl-5-(5-(morpholinomethyl)-1,3,4-oxadiazol-2-yl)pyridin-4-amine

HRID 595430

Reaction equation

HRID 595430 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])[C:5]([C:12]2[O:13][C:14]([CH2:17]Cl)=[N:15][N:16]=2)=[CH:4][N:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[I-].[K+]>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])[C:5]([C:12]2[O:13][C:14]([CH2:17][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:15][N:16]=2)=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 4875Potassium IodideHCID 8083MorpholineHCID 896908932-chloro-5-(5-(chloromethyl)-1,3,4-oxadiazol-2-yl)-N-isopropylpyridin-4-amine

Product 1

HCID 896897432-chloro-N-isopropyl-5-(5-(morpholinomethyl)-1,3,4-oxadiazol-2-yl)pyridin-4-amine

Procedure

2-chloro-5-(5-(chloromethyl)-1,3,4-oxadiazol-2-yl)-N-isopropylpyridin-4-amine (46) (60 mg, 0.2 mmol) was taken in a rbf, added morpholine (4 mL) to the rbf followed by the addition of potassium iodide (0.2 mmol), stirred the reaction mixture overnight at room temperature. The reaction mixture was concentrated under reduced pressure to remove excess of morpholine. The crude material obtained was taken to next step as such, without purification. LC/MS: Purospher@star RP-18, 4×55 mm, 3 μm; Solvent A=10% ACN: 90% H2O: 20 mM NH4OAc; Solvent B=90% ACN: 10% H2O: 20 mM NH4COOAc; gradient 0-100% B over 1.5 min (3.2 min run time); retention time: 1.608 min; LCMS (ES-API), m/z 338.2 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove excess of morpholine

Sources & evidence

ORD record
ord-f5b3a537fefe4907ae8f3928ee2301d4
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Linked notes

Loading…