Methyl 6-aminonicotinate → HCID 44465843, compound

HRID 2381477Notes

Reaction equation

HRID 2381477 reaction equation
[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[CH:13]=[N:12]2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26][O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[N:31][CH:30]=1>>[CH3:26][O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:8](=[O:9])[CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[CH:13]=[N:12]2)[CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:31][CH:30]=1

Participants

3

Reactant 2

HCID 737487Methyl 6-aminonicotinateHCID 57919284HCID 57919284, compound2×

Product 1

HCID 44465843HCID 44465843, compoundYield 32%

Procedure

Using the method described in Example 66, 3-cyclopentyl-2-(6-oxo-4-o-tolyloxy-6H-pyridazin-1-yl)-propionic acid (Intermediate 41) and 6-amino-nicotinic acid methyl ester afforded 6-[3-cyclopentyl-2-(6-oxo-4-o-tolyloxy-6H-pyridazin-1-yl)-propionylamino]-nicotinic acid methyl ester as a yellow solid (230 mg, 32%); ESI-LRMS m/e calcd for C26H28N4O5 [M+] 477, found 477 [M+H+]. 1H-NMR (300 MHz, DMSO-d6) δ ppm 0.95-1.25 (m, 1H) 1.31-1.81 (m, 8H) 1.85-2.07 (m, 1H) 2.16 (s, 3H) 2.21-2.41 (m, 1H) 3.85 (s, 3H) 5.51-5.60 (m, 1H) 5.58 (d, J=2.8 Hz, 1H) 7.22 (dd, J=7.5, 1.5 Hz, 1H) 7.24-7.38 (m, 2H) 7.38-7.45 (m, 1H) 8.11 (d, J=8.8 Hz, 1H) 8.19 (d, J=2.8 Hz, 1H) 8.27 (dd, J=8.8, 2.4 Hz, 1H) 8.87 (d, J=2.4 Hz, 1H) 11.39 (s, 1H).

Sources & evidence

ORD record
ord-235ce39400b6413dac348a9db7bc5722
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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