HCID 57919304, compound → HCID 57919264, compound

HRID 2381447Notes

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[C:25]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:26])[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]=[CH:21][C:20]=3[C:25]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:26])[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])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 57919304HCID 57919304, compound2×

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

Product 1

HCID 57919264HCID 57919264, compoundYield 19%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-{6-oxo-4-[2-(pyrrolidine-1-carbonyl)-phenoxy]-6H-pyridazin-1-yl}-propionic acid (Intermediate 27) 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-[2-(pyrrolidine-1-carbonyl)-phenoxy]-6H-pyridazin-1-yl}-propionamide as a light yellow solid (24.6 mg, 19%); ES+-HRMS m/e calcd for C30H38N6O5 [M+H+] 563.2977 found 563.2974. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.03-1.08 (m, 7H) 1.25-2.03 (m, 13H) 2.19-2.40 (m, 1H) 3.21 (t, J=6.2 Hz, 2H) 3.28-3.36 (m, 2H) 3.89 (s, 2H) 4.67 (s, 1H) 5.47 (dd, J=11.1, 4.3 Hz, 1H) 5.79 (d, J=2.8 Hz, 1H) 6.40 (d, J=2.1 Hz, 1H) 7.38 (d, J=8.1 Hz, 1H) 7.41 (t, J=7.5 Hz, 1H) 7.49-7.54 (m, 2H) 7.54-7.61 (m, 1H) 8.07 (d, J=2.8 Hz, 1H) 10.80 (s, 1H).

Sources & evidence

ORD record: ord-cf4b89f87f0b46e4a47b8c814c71f757
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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