2-Amino-5-methylpyridine → HCID 16663093, compound

HRID 2402305Notes

Reaction equation

HRID 2402305 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([CH2:11][CH2:12][C:13]([NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=O)=[CH:18][N:17]=1)=[O:14])[N:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:7]2=[O:33].CC1C=CC(N)=NC=1>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([CH2:11][CH2:12][C:13]([NH:15][C:16]1[CH:24]=[CH:23][C:19]([CH3:20])=[CH:18][N:17]=1)=[O:14])[N:8]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)[C:7]2=[O:33]

Participants

3

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 160587176-{3-[7-Fluoro-2-(4-fluorobenzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-nicotinic acid

Product 1

HCID 16663093HCID 16663093, compound

Procedure

The product from Example 11, Part D (120 mg, 0.36 mmol) and 5-methylpyridin-2-ylamine (39 mg, 0.36 mmol) were converted to the title compound in a manner analogous to the method described in Example 27 (78 mg, 50%). 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.99 (d, J=8 Hz, 1H), 7.94 (s, 1H), 7.66 (d, J=7 Hz, 1H), 7.49 (dd, J=8 Hz, 2 Hz, 1H), 7.43 (m, 1H), 7.30 (m, 2H), 7.17 (t, J=9 Hz, 1H), 7.00 (t, J=7 Hz, 2H), 5.26 (d, J=15 Hz, 1H), 4.68 (m, 1H), 4.21 (d, J=15 Hz, 1H), 2.55 (m, 2H), 2.27 (s, 3H), 1.92 (m, 2H). MS: m/z (MH+) 422.

Sources & evidence

ORD record
ord-3b64ee7343df4e27be7274d1f237f083
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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