(+/-)-2-(4-Fluoro-1-(3-nitropyridin-4-yl)piperidin-3-yl)isoindoline-1,3-dione → HCID 69090590, compound

HRID 69905Notes

Reaction equation

HRID 69905 reaction equation
[F:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:4][CH:3]1[N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:27]>C(O)C.C(OCC)(=O)C>[NH2:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[N:5]1[CH2:6][CH2:7][CH:2]([F:1])[CH:3]([N:17]2[C:18](=[O:27])[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]2=[O:26])[CH2:4]1

Participants

4

Reactant 1

HCID 77419824(+/-)-2-(4-Fluoro-1-(3-nitropyridin-4-yl)piperidin-3-yl)isoindoline-1,3-dione

Product 1

HCID 69090590HCID 69090590, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following Method 2 of Example 49, (+/−)-2-(4-fluoro-1-(3-nitropyridin-4-yl)piperidin-3-yl)isoindoline-1,3-dione in ethanol and ethyl acetate (1:1, 0.1 M solution) was reduced yielding (+/−)-2-(1-(3-aminopyridin-4-yl)-4-fluoropiperidin-3-yl)isoindoline-1,3-dione, (87%). LCMS (m/z): 341.1 (MH+); LC Rt=2.23 min.

Sources & evidence

ORD record
ord-ed959042dfce45a48228793c4eab4849
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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