HCID 57919097, compound → HCID 44464304, compound

HRID 2381448Notes

Reaction equation

HRID 2381448 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([OH:15])=O)[C:9](=[O:11])[CH:10]=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>>[OH:34][C:32]([CH3:35])([CH3:33])[CH2:31][N:28]1[CH:29]=[CH:30][C:26]([NH:25][C:13](=[O:15])[CH:12]([N:8]2[C:9](=[O:11])[CH:10]=[C:5]([O:4][C:3]3[C:2]([F:1])=[CH:23][CH:22]=[CH:21][C:20]=3[F:24])[CH:6]=[N:7]2)[CH2:16][CH:17]([CH3:19])[CH3:18])=[N:27]1

Participants

3

Reactant 2

HCID 57919097HCID 57919097, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 44464304HCID 44464304, compoundYield 45%

Procedure

Using the method described in Example 17, 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-methyl-pentanoic acid (Intermediate 28) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-methyl-pentanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide as a white solid (0.63 g, 45%); ES+-HRMS m/e calcd for C23H27N5O4F2 [M+H+] 476.2104 found 476.2104. 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.87 (d, J=6.6 Hz, 3H) 0.89 (d, J=6.6 Hz, 3H) 1.05 (s, 3H) 1.07 (s, 3H) 1.44 (br s, 1H) 1.73-1.86 (m, 1H) 2.11-2.27 (m, 1H) 3.89 (s, 2H) 4.67 (s, 1H) 5.53 (dd, J=11.2, 4.4 Hz, 1H) 6.04 (d, J=3.0 Hz, 1H) 6.40 (d, J=2.3 Hz, 1H) 7.34-7.44 (m, 2H) 7.44-7.52 (m, 1H) 7.53 (d, J=2.3 Hz, 1H) 8.28 (d, J=3.0 Hz, 1H) 10.85 (s, 1H).

Sources & evidence

ORD record
ord-1ffe81dbc9354d6e8cc9df0f6ab9df87
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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