Morpholine → HCID 136043091, compound

HRID 915963Notes

Reaction equation

HRID 915963 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:24])[C:11]3[C:16]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:15][N:14]([CH3:23])[C:12]=3[N:13]=2)=[C:4]([O:25][CH3:26])[CH:3]=1.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>O.ClCCl>[CH:17]1([C:16]2[C:11]3[C:10](=[O:24])[NH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:28]([N:46]5[CH2:51][CH2:50][O:49][CH2:48][CH2:47]5)=[O:30])=[CH:3][C:4]=4[O:25][CH3:26])=[N:13][C:12]=3[N:14]([CH3:23])[N:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 1359488876-(4-Amino-2-methoxyphenyl)-3-cyclohexyl-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 136043091HCID 136043091, compoundYield 215.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 3 ml dichloromethane suspension of 100 mg (0.283 mmol) of the compound obtained in Example 44, 28 mg (0.0944 mmol) of triphosgene and 79 μl (0.566 mmol) of triethylamine were added, and the mixture was stirred at room temperature for 15 minutes. Then, 25 μl (0.283 mmol) of morpholine was added to the reaction mixture, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=15/1) to obtain 95 mg (72%) of the captioned compound.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-fe7bc71074694cfa9415e2457703389c
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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