Triphenylphosphine → HCID 58530768, compound

HRID 2400891Notes

Reaction equation

HRID 2400891 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12](/[CH:16]=[C:17]4/[C:18](=[O:24])[N:19]([OH:23])[C:20](=[O:22])[S:21]/4)=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:27]([F:30])([F:29])[F:28])[CH:3]=1.O[CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.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>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12](/[CH:16]=[C:17]4/[C:18](=[O:24])[N:19]([O:23][CH2:32][CH2:33][N:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[C:20](=[O:22])[S:21]/4)=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:27]([F:28])([F:30])[F:29])[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 762881-PyrrolidineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 58530569HCID 58530569, compound

Product 1

HCID 58530768HCID 58530768, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-3-hydroxy-1,3-thiazolidine-2,4-dione (Example 288; 0.044 mmol), 1-(2-hydroxyethyl)pyrrolidine (1.5 equiv.) and triphenylphosphine (1.5 equiv.) in THF (5 mL) was added DIAD (1.5 equiv.) and the resultant solution was stirred overnight at rt. The mixture was then concentrated in vacuo, and the residue was purified by reverse phase HPLC (MeCN/water/formic acid) to provide (5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-3-(2-pyrrolidin-1-ylethoxy)-1,3-thiazolidine-2,4-dione.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue was purified by reverse phase HPLC (MeCN/water/formic acid)

Sources & evidence

ORD record
ord-0493987b5f844a408db4a9d1b39efcfe
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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