Triphenylphosphine → HCID 89870951, compound

HRID 516155Notes

Reaction equation

HRID 516155 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]#[C:12][C:13]2[C:21]3[C:16](=[N:17][CH:18]=[N:19][C:20]=3[NH2:22])[NH:15][N:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C:23]([C@@H:25]1[CH2:29][C@@H:28](O)[CH2:27][N:26]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])#[CH:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[NH2:22][C:20]1[N:19]=[CH:18][N:17]=[C:16]2[N:15]([C@@H:28]3[CH2:27][N:26]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[C@H:25]([C:23]#[CH:24])[CH2:29]3)[N:14]=[C:13]([C:12]#[C:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)[C:21]=12

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11816659tert-butyl (2S,4R)-2-ethynyl-4-hydroxypyrrolidine-1-carboxylateHCID 178489940HCID 178489940, compound

Product 1

HCID 89870951HCID 89870951, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-((3,5-Dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (14 mg) obtained in Example 1 (Step 1), (2S,4R)-tert-butyl 2-ethynyl-4-hydroxypyrrolidine-1-carboxylate (15 mg) synthesized by the method disclosed in WO2005/007083, and triphenylphosphine (23 mg) were suspended in THF (1.0 ml). DIAD (18 μl) was added to the suspension, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated and dissolved in a solution of DMSO. The resulting solution was purified by preparative reversed-phase HPLC purification (water/acetonitrile (0.1% formic acid)) to obtain the title compound as a colorless, amorphous substance (5.0 mg). Physical properties: m/z [M+H]+ 489.2

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in a solution of DMSO
  3. customThe resulting solution was purified by preparative reversed-phase HPLC purification (water/acetonitrile (0.1% formic acid))

Sources & evidence

ORD record
ord-256914c463134593a35265e4566f99ad
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

Loading…