3-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole → (R)-1-[4-(6-fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-3-(3-isoxazolo[5,4-b]pyridin-3-yl-phenoxy)-propan-2-ol

HRID 852188Notes

Reaction equation

HRID 852188 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1.[F:21][C:22]1[CH:36]=[CH:35][C:25]2[C:26]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[N:27][O:28][C:24]=2[CH:23]=1>CN(C)C=O.C(O)C>[F:21][C:22]1[CH:36]=[CH:35][C:25]2[C:26]([CH:29]3[CH2:30][CH2:31][N:32]([CH2:3][C@@H:2]([OH:1])[CH2:4][O:5][C:6]4[CH:11]=[CH:10][CH:9]=[C:8]([C:12]5[C:20]6[C:15](=[N:16][CH:17]=[CH:18][CH:19]=6)[O:14][N:13]=5)[CH:7]=4)[CH2:33][CH2:34]3)=[N:27][O:28][C:24]=2[CH:23]=1

Participants

5

Reactant 2

HCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 58928270(R)-3-(3-oxiranylmethoxy-phenyl)-isoxazolo[5,4-b]pyridine

Product 1

HCID 58928265(R)-1-[4-(6-fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-3-(3-isoxazolo[5,4-b]pyridin-3-yl-phenoxy)-propan-2-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared from a mixture of (R)-3-(3-oxiranylmethoxy-phenyl)-isoxazolo[5,4-b]pyridine in dimethylformamide and ethanol and 6-fluoro-3-piperidine-4-yl-benzo[d]isoxazole (Table No. 1, SM 8) in ethanol essentially as described above in Example 102. Purity by LC/MS=100%, [M+H]+=489.

Sources & evidence

ORD record
ord-56b495354df641ff9bd2a6247d5751d9
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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