2-Amino-5-chloropyridine → HCID 58869804, compound

HRID 2402307Notes

Reaction equation

HRID 2402307 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].NC1C=CC([Cl:41])=CN=1>>[Cl:41][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:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[N:17][CH:18]=1

Participants

3

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 160587176-{3-[7-Fluoro-2-(4-fluorobenzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-nicotinic acid

Product 1

HCID 58869804HCID 58869804, compound

Procedure

The product of Example 11, Part D (120 mg, 0.45 mmol) and 2-amino-5-chloropyridine (58 mg, 0.45 mmol) were converted to the title compound in a manner analogous to the method described in Example 27 (85 mg, 49%). 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 8.09 (d, J=8.7 Hz, 1H), 7.81 (s, 1H); 7.69-7.61 (m, 3H); 7.48-7.43 (m, 1H); 7.35 (m, 2H), 7.26 (t, J=8.8 Hz, 1H); 7.17 (t, J=8.5 Hz, 2H); 5.28 (d, J=15 Hz, 1H), 4.69 (s, 1H), 4.26 (d, J=15 Hz, 1H), 2.59-2.48 (m, 2H); 1.98-1.90 (m, 2H). MS: m/z (MH+) 443.

Sources & evidence

ORD record
ord-8aae6c9ab1e1402bbfac2fb194e277aa
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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