Trifluoroacetic acid → 1-(3-{[7-Propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)pyrrolidine-2,5-dione

HRID 1245310Notes

Reaction equation

HRID 1245310 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=[O:7].[CH2:8]([C:11]1[C:19]2[O:18][N:17]=[C:16]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]=2[CH:14]=[CH:13][C:12]=1[O:25][CH2:26][CH2:27][CH2:28]Br)[CH2:9][CH3:10].C([O-])([O-])=O.[Cs+].[Cs+].C(O)(C(F)(F)F)=O>CN(C=O)C.O>[CH2:8]([C:11]1[C:19]2[O:18][N:17]=[C:16]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]=2[CH:14]=[CH:13][C:12]=1[O:25][CH2:26][CH2:27][CH2:28][N:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=[O:7])[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 11439SuccinimideHCID 219110397-Propyl-3-neopentyl-6-(3-bromopropyloxy)-1,2-benzisoxazole

Product 1

HCID 99774431-(3-{[7-Propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)pyrrolidine-2,5-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Pyrrolidine-2,5-dione (17 mg, 0.172 mmol) and 7-propyl-3-neopentyl-6-(3-bromopropyloxy)-1,2-benzisoxazole, from Example 9 above, (42 mg, 0.114 mmol) were combined in DMF (7 ml) with Cs2CO3 (56 mg, 0.17 mmol) at room temperature. The mixture was stirred 18 hours. The mixture was diluted with 2 ml H2O and acidified with TFA. The resulting mixture was purified by elution from a RP-18 reversed phase HPLC column with a 90:10 to 0:100 H2O:CH3CN gradient to yield 1-(3-{[7-propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)pyrrolidine-2,5-dione.

Workup

  1. customThe resulting mixture was purified by elution from a RP-18

Sources & evidence

ORD record
ord-33267f26772144548b5809c17af021aa
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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