Methyl 6-aminonicotinate → HCID 44466098, compound

HRID 2381478Notes

Reaction equation

HRID 2381478 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[F:25])[CH:13]=[N:12]2)[C:8]([OH:10])=O)[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:10])[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[F:25])[CH:13]=[N:12]2)[CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[N:31][CH:30]=1

Participants

3

Reactant 2

HCID 737487Methyl 6-aminonicotinateHCID 57919288HCID 57919288, compound2×

Product 1

HCID 44466098HCID 44466098, compoundYield 30%

Procedure

Using the method described in Example 66, 3-cyclopentyl-2-[4-(2-fluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 43) and 6-amino-nicotinic acid methyl ester afforded 6-{3-cyclopentyl-2-[4-(2-fluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionylamino}-nicotinic acid methyl ester as a yellow solid (200 mg, 30%); ESI-LRMS m/e calcd for C25H25F N4O5 [M+] 481, found 481 [M+H+]. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.00-1.21 (m, 1H) 1.26-1.84 (m, 8H) 1.87-2.05 (m, 1H) 2.22-2.40 (m, 1H) 3.86 (s, 3H) 5.58 (dd, J=10.9, 4.2 Hz, 1H) 5.82 (d, J=2.8 Hz, 1H) 7.29-7.56 (m, 4H) 8.10 (d, J=9.0 Hz, 1H) 8.24 (d, J=2.8 Hz, 1H) 8.28 (dd, J=9.0, 2.3 Hz, 1H) 8.87 (d, J=2.3 Hz, 1H) 11.42 (s, 1H).

Sources & evidence

ORD record
ord-5f46b7805f3c43cab9700d2b1add52b0
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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