Morpholine → HCID 131728504, compound

HRID 1172535Notes

Reaction equation

HRID 1172535 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]([CH3:34])[C:14]2[O:20][C:19]3[C:21]([Cl:30])=[CH:22][C:23]([NH:25][C:26](=[O:29])[CH2:27]Cl)=[CH:24][C:18]=3[CH2:17][S:16](=[O:32])(=[O:31])[C:15]=2[CH:33]=1)=[O:10]>CN(C=O)C>[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:34])[C:14]2[O:20][C:19]3[C:21]([Cl:30])=[CH:22][C:23]([NH:25][C:26](=[O:29])[CH2:27][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:24][C:18]=3[CH2:17][S:16](=[O:32])(=[O:31])[C:15]=2[CH:33]=1)=[O:10]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 116336414-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 131728504HCID 131728504, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Morpholine (0.235 mL, 2.7 mmol) was added to a solution of Example 133 (0.6 g, 1.3 mmol) in DMF (8 mL). The reaction mixture was stirred at 120° C. for 4 h, concentrated, treated with water and the solid that precipitated was filtered, washed with water and purified using flash chromatography (silica gel, 1% methanol/chloroform) to obtain the title compound. Yield: 0.57 g, (85%); 1H NMR (DMSO-d6): δ 2.7 (s, 3H, CH3), 3.2 (s, 2H, CH2), 3.7 (t, 4H, 2CH2), 3.9 (s, 2H, CH2), 4.28 (s, 2H, CH2), 5.35 (s, 2H, CH2), 7.82 (d, 1H, Ar), 8.0 (s, 1H, Ar), 8.12 (s, 1H, Ar), 8.2 (s, 1H, Ar); MS: m/e (CI+) 495 (M+1).

Workup

  1. concentrationconcentrated
  2. additiontreated with water
  3. customthe solid that precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. custompurified

Sources & evidence

ORD record
ord-bd6e398cc5734e049f16e38471aaa203
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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