Morpholine → HCID 21094016, compound

HRID 729736Notes

Reaction equation

HRID 729736 reaction equation
CCN(CC)CC.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[O:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH:21]([C:30]2[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=2)[C:22](=[O:29])[NH:23][C:24]2[S:25][CH:26]=[CH:27][N:28]=2)[CH2:16][CH2:15]1>CN(C=O)C>[N:8]1([S:36]([C:33]2[CH:34]=[CH:35][C:30]([CH:21]([CH2:20][CH:17]3[CH2:18][CH2:19][O:14][CH2:15][CH2:16]3)[C:22]([NH:23][C:24]3[S:25][CH:26]=[CH:27][N:28]=3)=[O:29])=[CH:31][CH:32]=2)(=[O:38])=[O:37])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 21094066HCID 21094066, compound

Product 1

HCID 21094016HCID 21094016, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NEt3 (120 μL, 868 μmol) and morpholine (76 μL, 868 μmol) were added to a stirred solution of 4-[2-(tetrahydropyran-4-yl)-1-(thiazol-2-ylcarbamoyl)ethyl]benzenesulfonyl chloride (Preparation 59, 300 mg, 723 μmol) in anhydrous DMF (4 mL). After 10 min, the solvents were removed in vacuo, then the residue was taken up in CH2Cl2 (50 mL). The CH2Cl2 solution was washed with H2O (20 mL), 1M HCl (20 mL), H2O (20 mL), saturated aqueous Na2CO3 (20 mL), and brine (20 mL), before being dried (MgSO4). Filtration, solvent evaporation, and recrystallisation (CH2Cl2-IH) gave the title compound: RTA=3.15 min; m/z (ES+)=466.1 [M+H]+.

Workup

  1. customthe solvents were removed in vacuo
  2. washThe CH2Cl2 solution was washed with H2O (20 mL), 1M HCl (20 mL), H2O (20 mL), saturated aqueous Na2CO3 (20 mL), and brine (20 mL)
  3. dry with materialbefore being dried (MgSO4)
  4. filtrationFiltration, solvent evaporation, and recrystallisation (CH2Cl2-IH)

Sources & evidence

ORD record
ord-7d0caf515b154597b5fe1eda021b60ce
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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