Morpholine → HCID 57897904, compound

HRID 1693527Notes

Reaction equation

HRID 1693527 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:31][CH2:32][CH2:33]O)=[C:10]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.CS(Cl)(=O)=O.CCN(CC)CC.[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:31][CH2:32][CH2:33][N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)=[C:10]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11627630HCID 11627630, compound

Product 1

HCID 57897904HCID 57897904, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[5-(4-chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy]-ethanol (13 mg, 0.025 mmol, prepared in 84% yield as described in Example 5 except using ethylene glycol as solvent.) in anhydrous CH2Cl2 (0.5 mL) is added CH3SO2Cl (5 μL) followed by Et3N (20 μL). After the addition, the mixture is stirred at room temperature for 2 h. and morpholine (20 μL) is added. After the resulted mixture is stirred at 60° C. for 10 h. it is cooled down to room temperature and treated with water (4 mL) and extracted with EtOAc (3×3 mL). The organic layers are combined and concentrated. The residue is purified by preparative LC/MS to provide the titled compound 5-(4-chloro-phenyl)-6-(2,4-dichloro-phenyl)-4-(2-morpholin-4-yl-ethoxy)-1-phenyl-1H-pyrazolo[3,4-b]pyridine. HPLC-MS calculated for C30H25Cl3N4O2 (M+H+): 579.1. Found: 579.1.

Workup

  1. additionAfter the addition
  2. stirringAfter the resulted mixture is stirred at 60° C. for 10 h. it
  3. temperatureis cooled down to room temperature
  4. extractionextracted with EtOAc (3×3 mL)
  5. concentrationconcentrated
  6. customThe residue is purified by preparative LC/MS

Sources & evidence

ORD record
ord-57bb255758204fab93c9f667db21c75e
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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