Methyl 6-aminonicotinate → HCID 44466929, compound

HRID 2381475Notes

Reaction equation

HRID 2381475 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[C:28]4[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=4[CH:22]=[CH:21][CH:20]=3)[CH:13]=[N:12]2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:29][O:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[N:34][CH:33]=1>>[CH3:29][O:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:8](=[O:9])[CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[C:24]4[CH2:25][CH2:26][CH2:27][CH2:28][C:23]=4[CH:22]=[CH:21][CH:20]=3)[CH:13]=[N:12]2)[CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[N:34][CH:33]=1

Participants

3

Reactant 2

HCID 737487Methyl 6-aminonicotinateHCID 57919149HCID 57919149, compound2×

Product 1

HCID 44466929HCID 44466929, compoundYield 38%

Procedure

Using the method described in Example 66, 3-cyclopentyl-2-[6-oxo-4-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 39) and 6-amino-nicotinic acid methyl ester afforded 6-{3-cyclopentyl-2-[6-oxo-4-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-6H-pyridazin-1-yl]-propionylamino}-nicotinic acid methyl ester as an off-white solid (153 mg, 38%); ES+-HRMS m/e calcd for C29H32N4O5 [M+H+] 517.2446 found 517.2442. 1H-NMR (300 MHz, CDCl3) δ ppm 1.06-1.31 (m, 2H), 1.31-1.99 (m, 1H), 2.11-2.42 (m, 2H), 2.55 (br s, 2H), 2.81 (br s, 2H), 3.93 (s, 3H), 5.64 (t, J=7.4 Hz, 1H), 5.93 (s, 1H), 6.83 (d, J=7.7 Hz, 1H), 7.04 (d, J=7.7 Hz, 1H), 7.15 (t, J=7.7 Hz, 1H), 7.94 (s, 1H), 8.29 (s, 2H), 8.87 (s, 1H), 9.25 (br s, 1H).

Sources & evidence

ORD record
ord-800c63d157a7417abaccd7bc1adae45b
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…