HCID 57919189, compound → HCID 66893131, compound

HRID 2381427Notes

Reaction equation

HRID 2381427 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[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)[CH:13]=[N:12]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:29][C:30]1[CH:34]=[CH:33][N:32]([CH2:35][C:36]([CH3:39])([OH:38])[CH3:37])[N:31]=1>>[OH:38][C:36]([CH3:39])([CH3:37])[CH2:35][N:32]1[CH:33]=[CH:34][C:30]([NH:29][C:8](=[O:10])[CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)[CH:13]=[N:12]2)[CH2:6][CH2:1][CH2:5][CH2:4][CH2:3][CH3:2])=[N:31]1

Participants

3

Reactant 2

HCID 57919189HCID 57919189, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 66893131HCID 66893131, compoundYield 11%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[4-(naphthalen-1-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 38) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 2-[4-(naphthalen-1-yloxy)-6-oxo-6H-pyridazin-1-yl]-octanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide as a white solid (0.15 g, 11%); ES+-HRMS m/e calcd for C29H33N5O4 [M+H+] 516.2606 found 516.2604. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.10-1.20 (br.s., 7H), 1.22-1.83 (m, 8H), 1.93 (m, 1H), 2.29 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 5.45 (m, 1H), 5.63 (s, 1H), 6.40 (s, 1H), 7.44-7.74 (m, 5H), 7.87-8.16 (m, 3H), 8.29 (s, 1H), 10.79 (s, 1H).

Sources & evidence

ORD record
ord-044ef3064a1f426489ad929472b570fe
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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