Morpholine → 7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(4-morpholinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889069Notes

Reaction equation

HRID 1889069 reaction equation
Br[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=3[Cl:23])=[O:12])[CH2:10][C:5]2=[N:4][N:3]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[Cl:23][C:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]([N:9]1[CH2:8][CH2:7][N:6]2[C:2]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[N:3][N:4]=[C:5]2[CH2:10]1)=[O:12]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 665992213-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 665989707-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(4-morpholinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Conditions

Temperature
110 °C

Procedure

3-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.075 g, 0.183 mmol, e.g. see Example 1 for methods of preparation) was treated with morpholine (1.5 mL) and heated in a microwave reactor at 110° C. for a total of 7 hours. The solvent was evaporated under reduced vacuum and the residue was purified by mass-directed automated (preparative) HPLC (MDAP) and triturated with isohexane to afford 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(4-morpholinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.012 g) as white solid.

Workup

  1. customThe solvent was evaporated under reduced vacuum
  2. customthe residue was purified
  3. customtriturated with isohexane

Sources & evidence

ORD record
ord-e49aeb0f442a431eba687ad5e66bcb18
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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