Morpholine → 3-(3-Morpholin-4-YL-pyrazin-2-YL)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1850245Notes

Reaction equation

HRID 1850245 reaction equation
Cl[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>>[C:15]([O:14][C:12]([N:10]1[CH2:11][CH:8]([C:3]2[C:2]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 59351411Tert-butyl 3-(3-chloropyrazin-2-yl)azetidine-1-carboxylate

Product 1

HCID 585473733-(3-Morpholin-4-YL-pyrazin-2-YL)-azetidine-1-carboxylic acid tert-butyl esterYield 94%

Conditions

Temperature
160 °C

Procedure

A mixture of 3-(3-chloro-pyrazin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (7) (269 mg, 1.0 mmol) in morpholine was heated by microwave at 160° C. for 2 h. The mixture was concentrated to give the crude compound and which was purified by column chromatography to afford pure product (11) (300 mg, yield 94%) as solid. ESI-MS (M+1): 321 calc. for C16H24N4O3 320.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give the crude compound and which
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-de35fc1c3c9044e5b3063a860d80c8fe
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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