HCID 57919123, compound → HCID 57919140, compound

HRID 2381441Notes

Reaction equation

HRID 2381441 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[N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:13]=[N:12]2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:31][C:32]1[CH:36]=[CH:35][N:34]([CH2:37][C:38]([CH3:41])([OH:40])[CH3:39])[N:33]=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]=[CH:21][C:20]=3[N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:13]=[N:12]2)[C:8]([NH:31][C:32]2[CH:36]=[CH:35][N:34]([CH2:37][C:38]([OH:40])([CH3:39])[CH3:41])[N:33]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 57919123HCID 57919123, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 57919140HCID 57919140, compoundYield 51%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[4-(2-morpholin-4-yl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 53) 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-[4-(2-morpholin-4-yl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionamide as a white solid (0.61 g, 51%); ES+-HRMS m/e calcd for C29H38N6O5 [M+H+] 551.2977 found 551.2976. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.08 (m, 1H), 1.24-1.76 (m, 8H), 1.92 (m, 1H), 2.28 (m, 1H), 2.83-3.05 (m, 4H), 3.46-3.59 (m, 4H), 3.89 (s, 2H), 4.67 (s, 1H), 5.51 (dd, J=4.1, J=11.0 Hz, 1H), 5.74 (d, J=3.0 Hz, 1H), 6.39 (d, J=2.1 Hz, 1H), 7.09-7.18 (m, 2H), 7.25 (dd, Jo=7.8 Hz, Jm=1.5 Hz, 1H), 7.27-7.37 (m, 1H), 7.52 (d, J=2.1 Hz, 1H), 8.02 (d, J=3.0 Hz, 1H), 10.77 (s, 1H).

Sources & evidence

ORD record
ord-5f9eb626ff8f45d882180982793613a4
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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