Morpholine → HCID 131728510, compound

HRID 1927532Notes

Reaction equation

HRID 1927532 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:32])[C:14]2[O:20][C:19]3[C:21]([NH:25][CH2:26][CH2:27]Cl)=[CH:22][CH:23]=[CH:24][C:18]=3[CH2:17][S:16](=[O:30])(=[O:29])[C:15]=2[CH:31]=1)=[O:10]>CN(C)C=O>[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:32])[C:14]2[O:20][C:19]3[C:21]([NH:25][CH2:26][CH2:27][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:22][CH:23]=[CH:24][C:18]=3[CH2:17][S:16](=[O:29])(=[O:30])[C:15]=2[CH:31]=1)=[O:10]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 131728511HCID 131728511, compound

Product 1

HCID 131728510HCID 131728510, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Morpholine (0.2 mL, 2.52 mmol) was added to a solution of Example 160 (0.5 g, 1.26 mmol) in dry dimethylformamide (10 mL) and the reaction mixture was stirred at 110° C. for 3 h. It was concentrated, treated with water and the solid that precipitated was filtered, washed with water, dried and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.5 g, (88.80%); 1H NMR (DMSO-d6): δ 2.35-2.45 (m, 4H, 2CH2), 2.60-2.70 (m, 4H, 2CH2), 2.80 (s, 3H, CH3), 3.10-3.20 (m, 2H, CH2), 3.55-3.60 (m, 2H, CH2), 3.90 (s, 3H, OCH3), 5.10 (s, 2H, CH2), 6.70-6.85 (m, 2H, Ar), 7.20 (t, 1H, Ar), 8.10 (s, 1H, Ar), 8.25 (s, 1H, Ar); MS: m/e (EI+) 446 (M+1).

Workup

  1. concentrationIt was concentrated
  2. additiontreated with water
  3. customthe solid that precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried
  7. custompurified

Sources & evidence

ORD record
ord-4a9eb61f603b408aa04ab7fdc13f454c
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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