Morpholine → HCID 89690940, compound

HRID 877587Notes

Reaction equation

HRID 877587 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([O:15]C)=O)=[N:10][N:9]=2)=[C:4]([NH:17][CH:18]([CH3:20])[CH3:19])[CH:3]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:15])=[N:10][N:9]=2)=[C:4]([NH:17][CH:18]([CH3:20])[CH3:19])[CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 89690969HCID 89690969, compound

Product 1

HCID 89690940HCID 89690940, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazole-2-carboxylate (66) (150 mg, 0.51 mmol) in morpholine (1 mL) and MeOH (1 mL) was heated at 80° C. for 2 h. The reaction mass was concentrated under reduced pressure. The crude material obtained was triturated with diethyl ether and filtered to get the desired compound, (5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2-yl)(morpholino)methanone. LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 0.88 min; LCMS (ES-API), m/z 352.7 (M+H).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customThe crude material obtained
  3. customwas triturated with diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c758106e2cb54f10bb09789d5fd9d57a
Source dataset
uspto-grants-2015_03
Patent number
US08987311B2

Reaction notes

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