Dimethylformamide → (R)-2-{4-[2-hydroxy-3-(3-isoxazolo[5,4-b]pyridin-3-yl-phenoxy)-propyl]-piperazin-1-yl}-benzonitrile

HRID 852187Notes

Reaction equation

HRID 852187 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.[CH3:21][N:22]([CH3:25])[CH:23]=O>C(O)C.C(C1C=CC=CC=1N1CCNCC1)#N>[OH:1][C@@H:2]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[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:7]=1)[CH2:3][N:16]1[CH2:17][CH2:23][N:22]([C:25]2[CH:10]=[CH:11][CH:6]=[CH:7][C:8]=2[C:12]#[N:13])[CH2:21][CH2:15]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 58928270(R)-3-(3-oxiranylmethoxy-phenyl)-isoxazolo[5,4-b]pyridine

Product 1

HCID 58928309(R)-2-{4-[2-hydroxy-3-(3-isoxazolo[5,4-b]pyridin-3-yl-phenoxy)-propyl]-piperazin-1-yl}-benzonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 2735875N-(2-Cyanophenyl)piperazineSolvent

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 1-(2-cyanophenyl)piperazine in ethanol essentially as described above in Example 102. Purity by LC/MS=100%, [M+H]+=456.

Sources & evidence

ORD record
ord-6749c9daabaa4597bffbaea5573e8e5d
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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