1-(2-Pyrimidinyl)piperazine → (R)-1-(3-isoxazolo[5,4-b]pyridin-3-yl-phenoxy)-3-(4-pyrimidin-2-yl-piperazin-1-yl)-propan-2-ol

HRID 852186Notes

Reaction equation

HRID 852186 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.[N:21]1([C:27]2[N:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CN(C)C=O.C(O)C>[O:14]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:20]2[C:12]([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[O:5][CH2:4][C@H:2]([OH:1])[CH2:3][N:24]2[CH2:25][CH2:26][N:21]([C:27]3[N:28]=[CH:29][CH:30]=[CH:31][N:32]=3)[CH2:22][CH2:23]2)=[N:13]1

Participants

5

Reactant 2

HCID 887471-(2-Pyrimidinyl)piperazineHCID 58928270(R)-3-(3-oxiranylmethoxy-phenyl)-isoxazolo[5,4-b]pyridine

Product 1

HCID 58928310(R)-1-(3-isoxazolo[5,4-b]pyridin-3-yl-phenoxy)-3-(4-pyrimidin-2-yl-piperazin-1-yl)-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 2-piperazin-1-yl-pyrimidine in ethanol essentially as described above in Example 102. Purity by LC/MS=100%, [M+H]+=433.

Sources & evidence

ORD record
ord-abf2464674ac408b8922092a71ee2ef7
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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