2-Amino-5-cyanopyridine → HCID 58869822, compound

HRID 2402310Notes

Reaction equation

HRID 2402310 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].[NH2:34]C1C=CC(C#N)=CN=1>>[C:20]([C:19]1[CH:23]=[CH:24][C:16]([NH:15][C:13](=[O:14])[CH2:12][CH2:11][CH:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])[C:7](=[O:33])[N:8]2[CH2:25][C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)=[N:17][CH:18]=1)#[N:34]

Participants

3

Reactant 2

HCID 8182602-Amino-5-cyanopyridineHCID 160587176-{3-[7-Fluoro-2-(4-fluorobenzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-nicotinic acid

Product 1

HCID 58869822HCID 58869822, compound

Procedure

The product of Example 11, Part D (113 mg, 0.34 mmol) and 2-amino-5-cyanopyridine (41 mg, 0.34 mmol) were converted to the title compound in a manner analogous to the method described in Example 27 (61 mg, 41%). 1H NMR (400 MHz, CDCl3) δ 8.48 (broad s, 1H); 8.24 (d, J=8.6 Hz, 1H), 7.92 (d, J=8.7 Hz, 1H), 7.82 (broad s, 1H), 7.70 (d, J=7.6 Hz, 1H); 7.49-7.45 (m, 1H), 7.33 (m, 2H), 7.23 (t, J=8.6 Hz, 1H); 7.04 (t, J=8.5 Hz, 2H); 5.24 (d, J=15 Hz, 1H), 4.72 (m, 1H), 4.28 (d, J=15 Hz, 1H), 2.61-2.56 (m, 1H); 2.53-2.46 (m, 1H); 2.00-1.95 (m, 2H). MS: m/z (MH+) 433.

Sources & evidence

ORD record
ord-0d7bd9576a664470ac009f5af1453bb8
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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