Water → HCID 23144159, compound

HRID 337455Notes

Reaction equation

HRID 337455 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[S:13][C:12]([NH2:14])=[N:11][C:10]=1[C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)=[O:8].[C:20]([N:27]1[CH:31]=[CH:30]N=[CH:28]1)(N1C=CN=C1)=[O:21].N1CC[O:35][CH2:34]C1.O>ClCCl>[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:10]1[N:11]=[C:12]([NH:14][C:20]([N:27]2[CH2:31][CH2:30][O:35][CH2:34][CH2:28]2)=[O:21])[S:13][C:9]=1[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 23144251HCID 23144251, compound

Product 1

HCID 23144159HCID 23144159, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 186 (100 mg, 0.369 mmol) was suspended in dichloromethane (3.7 mL), and carbonyldiimidazole (89.7 mg, 554 mmol) was added thereto at room temperature, followed by stirring for 12 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in THF (3.7 mL). Morpholine (0.0484 mL, 554 mmol) was added to the resulting solution, followed by stirring for 2 hours at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=20:1) to afford the entitled Compound 256 (93.9 mg, 66%) as a pale yellow solid.

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in THF (3.7 mL)
  4. stirringby stirring for 2 hours at room temperature
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-8ed2d7671350484cad42b7bce062b38a
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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