Morpholine → HCID 117770349, compound

HRID 1526280Notes

Reaction equation

HRID 1526280 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:4][N:3]=1.ON1C2C=CC=CC=2N=N1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:11])[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 24729521(2-Chloropyridin-4-yl)acetic acid

Product 1

HCID 117770349HCID 117770349, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of (2-chloropyridin-4-yl)acetic acid (300 mg), 1-hydroxybenzotriazole (284 mg), triethylamine (0.487 mL), morpholine (0.183 mL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (469 mg) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 18 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (239 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d9747be434184e62839931c2560046ff
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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