HCID 57919115, compound → HCID 44464555, compound

HRID 2381547Notes

Reaction equation

HRID 2381547 reaction equation
[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([S:18][C:19]3[CH:24]=[CH:23][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.[NH2:25][C:26]1[CH:30]=[CH:29][N:28]([CH2:31][C:32]([CH3:35])([OH:34])[CH3:33])[N:27]=1>>[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([S:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:13]=[N:12]2)[C:8]([NH:25][C:26]2[CH:30]=[CH:29][N:28]([CH2:31][C:32]([OH:34])([CH3:33])[CH3:35])[N:27]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 57919115HCID 57919115, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 44464555HCID 44464555, compound

Procedure

Using the method described in Example 49, 3-cyclopentyl-2-(6-oxo-4-phenylsulfanyl-6H-pyridazin-1-yl)-propionic acid (Intermediate 95) 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-phenylsulfanyl-6H-pyridazin-1-yl)-propionamide was obtained as an off-white solid (83.5 mg, 61%); ES+-HRMS m/e calcd for C25H31N5O3S [M+H+] 482.2221 found 482.2221. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04 (br. s., 3H), 1.05 (br. s., 3H), 1.19-1.78 (m, 9H), 1.78-2.00 (m, 1H), 2.10-2.32 (m, 1H), 3.88 (s, 2H), 4.67 (s, 1H), 5.42 (dd, J=10.9, 4.2 Hz, 1H), 5.95 (d, J=2.4 Hz, 1H), 6.38 (d, J=2.4 Hz, 1H), 7.52 (d, J=2.4 Hz, 1H), 7.56-7.70 (m, 5H), 7.94 (d, J=2.4 Hz, 1H), 10.79 (s, 1H).

Sources & evidence

ORD record
ord-f337724476e942f2bd4a08952b4674e5
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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