Morpholine → HCID 46208937, compound

HRID 555813Notes

Reaction equation

HRID 555813 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24](Cl)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>CS(C)=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 59351413HCID 59351413, compound

Product 1

HCID 46208937HCID 46208937, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of benzo[d]thiazol-2-yl(4-(3-chloropyrazin-2-yloxy)phenyl)methanone (185 mg, 0.503 mmol) in DMSO (2 mL) was added morpholine (219 μl, 2.52 mmol). The reaction mixture was heated at 100° C. for 2 h. The reaction mixture was partitioned between EtOAc and brine. The precipitate formed was collected by filtration, washed with EtOAc and water, dried to provide benzo[d]thiazol-2-yl(4-(3-morpholinopyrazin-2-yloxy)phenyl)methanone as light-yellow solid. MS (ESI, pos. ion) m/z: 419.0. IC50 (uM) ++.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and brine
  2. customThe precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed with EtOAc and water
  5. customdried

Sources & evidence

ORD record
ord-8bfe9f3cd53b4a77b2e4afbe198e0dee
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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