Morpholine → HCID 21094016, compound

HRID 1350328Notes

Reaction equation

HRID 1350328 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-7dbd0a7aa7d04c889e721528a42b395b
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

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