Morpholine → HCID 69312257, compound

HRID 271536Notes

Reaction equation

HRID 271536 reaction equation
[N:1]1([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]3[O:20][C:19]([C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)=[C:18]([C:27]4[CH:28]=[C:29]5[C:33](=[CH:34][CH:35]=4)[C:32](=NO)[CH2:31][CH2:30]5)[CH:17]=3)[CH2:11]2)=[O:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N1CC[O:41]CC1.C(N(CC)CC)C>ClCCl>[N:1]1([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]3[O:20][C:19]([C:21]4[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=4)=[C:18]([C:27]4[CH:28]=[C:29]5[C:33](=[CH:34][CH:35]=4)[C:32](=[O:41])[CH2:31][CH2:30]5)[CH:17]=3)[CH2:11]2)=[O:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 136355255HCID 136355255, compound

Product 1

HCID 69312257HCID 69312257, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product of Step 1 (140 mg, 0.32 mmol) in dry dichloromethane (10 ml) was treated with morpholine (0.031 ml, 0.35 mmol) and triethylamine (0.049 ml, 0.35 mmol) and heated at reflux for 3 hours. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried, concentrated in vacuo and then purified by silica gel chromatography eluting with chloroform/ethanol/0.880 ammonia solution (98:1.8:0.2) to yield the title compound (85 mg, 55%); MS(ES+) m/e 486 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography
  7. washeluting with chloroform/ethanol/0.880 ammonia solution (98:1.8:0.2)

Sources & evidence

ORD record
ord-f758c5d85ba24d28a375403c58608e30
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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