Thiazolidinedione → HCID 89189103, compound

HRID 2207526Notes

Reaction equation

HRID 2207526 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:24][CH2:25][CH2:26]O)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)[C:3]=12.[S:28]1[CH2:32][C:31](=[O:33])[NH:30][C:29]1=[O:34].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>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:24][CH2:25][CH2:26][N:30]3[C:31](=[O:33])[CH2:32][S:28][C:29]3=[O:34])[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)[C:3]=12

Participants

6

Reactant 4

HCID 5437ThiazolidinedioneHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 90313797HCID 90313797, compound

Product 1

HCID 89189103HCID 89189103, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propan-1-ol (0.5 g, 1.4 mmol, 1 eq.), thiazolidine-2,4-dione (0.20 g, 1.7 mmol, 1.2 eq.), triphenylphosphine (1.1 g, 4.2 mmol, 3.0 eq.) in THF (25 mL) in ice/water bath was added DIAD (0.85 mmol, 4.2 mmol, 3.0 eq.) dropwise. The resulting solution was stirred at this temperature for 0.5 h and then stirred at room temperature for another 2 h. The volatile phase was removed off under reduced pressure. The residue was applied on silica gel and eluted to give 3-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propyl)thiazolidine-2,4-dione (0.4 g, 62%) as an off-white solid.

Workup

  1. stirringstirred at room temperature for another 2 h
  2. customThe volatile phase was removed off under reduced pressure
  3. washeluted

Sources & evidence

ORD record
ord-8a60ec303d724687b07d15ab50a00a2f
Source dataset
uspto-grants-2016_06
Patent number
US09376438B2

Reaction notes

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