Triphenylphosphine → HCID 58200838, compound

HRID 1951058Notes

Reaction equation

HRID 1951058 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[N:27]=[CH:26][C:25]([OH:28])=[CH:24][N:23]=3)[CH:17]=2)[N:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:49]1[CH2:54][CH2:53][N:52]([CH2:55][CH2:56]O)[CH2:51][CH2:50]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[N:27]=[CH:26][C:25]([O:28][CH2:56][CH2:55][N:52]4[CH2:53][CH2:54][O:49][CH2:50][CH2:51]4)=[CH:24][N:23]=3)[CH:17]=2)[N:10]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58200826HCID 58200826, compound

Product 1

HCID 58200838HCID 58200838, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.2 A suspension of 108 mg (0.253 mmol) of 1-[3-(2,5-dichlorophenyl)-4,5-dihydropyrazol-1-yl]-2-[3-(5-hydroxypyrimidin-2-yl)phenyl]ethanone, 100 mg (0.38 mmol) of triphenylphosphine and 64.4 μl of 2-morpholinoethanol in 0.5 ml of THF is cooled in an ice bath, and 74 μl (0.38 mmol) of diisopropyl azodicarboxylate are slowly added dropwise. The reaction mixture is stirred at room temperature for 16 hours. The mixture is evaporated and the residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent: 1-[3-(2,5-dichlorophenyl)-4,5-dihydropyrazol-1-yl]-2-{3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]phenyl}-ethanone (“A8”) as colourless crystals; ESI 540;

Workup

  1. temperatureis cooled in an ice bath
  2. customThe mixture is evaporated
  3. customthe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-dba0295a649f470e9b6d79945a236f94
Source dataset
uspto-grants-2013_03
Patent number
US08404685B2

Reaction notes

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