HCID 57919227, compound → HCID 57919152, compound

HRID 2381416Notes

Reaction equation

HRID 2381416 reaction equation
[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:13]=[N:12]2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:24][C:25]1[CH:29]=[CH:28][N:27]([CH2:30][C:31]([CH3:34])([OH:33])[CH3:32])[N:26]=1>>[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:13]=[N:12]2)[C:8]([NH:24][C:25]2[CH:29]=[CH:28][N:27]([CH2:30][C:31]([OH:33])([CH3:32])[CH3:34])[N:26]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 57919227HCID 57919227, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 57919152HCID 57919152, compoundYield 23%

Procedure

Using the method described in Example 1, 3-cyclopentyl-2-(4-cyclopentyloxy-6-oxo-6H-pyridazin-1-yl)-propionic acid (Intermediate 61) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 3-cyclopentyl-2-(4-cyclopentyloxy-6-oxo-6H-pyridazin-1-yl)-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide (49.8 mg, 23%) as a white solid; ES+-HRMS m/e calcd for C24H35N5O4 [M+Na+] 480.2581, found 480.2582. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.05 (m, 1H), 1.25-1.80 (m, 14H), 1.83-2.00 (m, 3H), 2.28 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 4.86 (m, 1H), 5.45 (dd, J=4.3, J=11.1 Hz, 1H), 6.24 (d, J=2.8 Hz, 1H), 6.39 (d, J=2.3 Hz, 1H), 7.52 (d, J=2.3 Hz, 1H), 7.76 (d, J=2.8 Hz, 1H), 10.74 (s, 1H).

Sources & evidence

ORD record
ord-bc722f06618d42bf9ea998b8b7261c08
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…