6-{3-[7-Fluoro-2-(4-fluorobenzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-nicotinic acid → HCID 58869834, compound

HRID 2402311Notes

Reaction equation

HRID 2402311 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(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].[CH3:34][S:35](C1C=CC(N)=NC=1)(=[O:37])=[O:36]>>[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]([S:35]([CH3:34])(=[O:37])=[O:36])=[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]

Participants

3

Reactant 2

HCID 160587176-{3-[7-Fluoro-2-(4-fluorobenzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-nicotinic acidHCID 178610085-Methanesulfonylpyridin-2-amine

Product 1

HCID 58869834HCID 58869834, compound

Procedure

The product of Example 11, Part D (0.175 g, 0.529 mmol) and 5-Methanesulfonyl-pyridin-2-ylamine (91 mg, 0.529 mmol) were converted to the title compound in a manner analogous to the method described in Example 27 (159 mg, 62%). 1H NMR (400 MHz, CDCl3) d 8.74 (s, 1H); 8.30 (d, J=8.8 Hz, 1H), 8.18 (d, J=8.8 Hz, 1H), 8.09 (broad s, 1H), 7.69 (d, J=7 Hz, 1H); 7.49-7.44 (m, 1H), 7.33-7.30 (m, 2H), 7.23 (t, J=8.8 Hz, 1H); 7.04 (t, J=8.6 Hz, 2H); 5.25 (d, J=15 Hz, 1H), 4.73 (m, 1H), 4.28 (d, J=15 Hz, 1H), 3.18 (s, 3H); 2.61-2.59 (m, 1H); 2.53-2.50 (m, 1H); 2.04-1.97 (m, 2H). MS: m/z (MH+) 486.

Sources & evidence

ORD record
ord-6efce9a0c5c646569c9e14c698ba7a82
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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