Dimethylformamide → (R)-1-(benzyl-methyl-amino)-3-(3-isoxazolo[5,4-b]pyridin-3-yl-phenoxy)-propan-2-ol

HRID 852183Notes

Reaction equation

HRID 852183 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])C=O>C(O)C.CNCC1C=CC=CC=1>[CH2:21]([N:22]([CH3:25])[CH2:3][C@@H:2]([OH:1])[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)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

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

Product 1

HCID 9865144(R)-1-(benzyl-methyl-amino)-3-(3-isoxazolo[5,4-b]pyridin-3-yl-phenoxy)-propan-2-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 7669N-MethylbenzylamineSolvent

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 N-methylbenzylamine in ethanol essentially as described above in Example 102. Purity by LC/MS=100%, [M+H]+=390.

Sources & evidence

ORD record
ord-7c2426f1574b43e3b98855b59ee75e93
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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