2-Aminopyridine → 2-(1,3-dioxoisoindolin-2-yl)-4-methyl-N-(pyridin-2-yl)pentanamide

HRID 1677673Notes

Reaction equation

HRID 1677673 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:13]([NH:15][C:16]1S[CH:18]=[CH:19][N:20]=1)=[O:14].N[C:26]1[CH:31]=CC=CN=1>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:13]([NH:15][C:16]1[CH:31]=[CH:26][CH:18]=[CH:19][N:20]=1)=[O:14]

Participants

3

Reactant 2

HCID 104392-AminopyridineHCID 28317062-(1,3-dioxoisoindolin-2-yl)-4-methyl-N-(thiazol-2-yl)pentanamide

Product 1

HCID 248901242-(1,3-dioxoisoindolin-2-yl)-4-methyl-N-(pyridin-2-yl)pentanamide

Procedure

The title compound was synthesized according to the method described in connection with Compound 13, except that 2-aminopyridine was used. 1H NMR (400 MHz, MeOH-d4) δ: 8.34 (dd, J=1.2, 6.0 Hz, 1H), 8.12-8.17 (m, 1H), 7.91-7.94 (m, 2H), 7.85-7.88 (m, 2H), 7.79 (d, J=7.2 Hz, 1H), 7.38-7.43 (m, 1H), 5.19 (dd, J=4.4, 11.2 Hz, 1H) 2.35-2.44 (m, 1H), 1.97-2.06 (m, 1H), 1.51 (m, 1H) 1.0 (d, J=6.4 Hz, 3H), 0.97 (d, J=6.4 Hz, 3H). [M+H] calc'd for C19H19N3O3, 338. found, 338.

Sources & evidence

ORD record
ord-adf2104062de432bba94ae765f85f01e
Source dataset
uspto-grants-2011_08
Patent number
US08008332B2

Reaction notes

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