HCID 57919146, compound → HCID 57919305, compound

HRID 2381442Notes

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]=[C:21]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:20]=3)[CH:13]=[N:12]2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:32][C:33]1[CH:37]=[CH:36][N:35]([CH2:38][C:39]([CH3:42])([OH:41])[CH3:40])[N:34]=1>>[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]=[C:21]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:20]=3)[CH:13]=[N:12]2)[C:8]([NH:32][C:33]2[CH:37]=[CH:36][N:35]([CH2:38][C:39]([OH:41])([CH3:42])[CH3:40])[N:34]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Reactant 2

HCID 57919146HCID 57919146, compound2×

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

Product 1

HCID 57919305HCID 57919305, compoundYield 48%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[6-oxo-4-(3-phenoxy-phenoxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 49) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-[6-oxo-4-(3-phenoxy-phenoxy)-6H-pyridazin-1-yl]-propionamide as a white solid (0.63 g, 48%); ES+-HRMS m/e calcd for C31H35N5O5 [M+H+] 558.2711 found 558.2706. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.07 (m, 1H), 1.24-0-1.77 (m, 8H), 1.91 (m, 1H), 2.27 (m, 1H), 3.89 (s, 2H), 4.68 (s, 1H), 5.46 (dd, J=4.4, J=11.0 Hz, 1H), 5.89 (d, J=2.7 Hz, 1H), 6.39 (d, J=2.4 Hz, 1 Hr), 6.94 (m, 1H), 6.96 (d, Jm=1.5 Hz, 1H), 7.05 (m, 1H), 7.11 (dd, Jo=7.8 Hz, 2H), 7.19 (t, Jo=7.4 Hz, 1H), 7.38-7.55 (m, 4H), 8.10 (d, J=2.7 Hz, 1H), 10.79 (s, 1H).

Sources & evidence

ORD record: ord-6db6a66d3d044d0baee9d0067101a5b3
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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