HCID 57919339, compound → HCID 44464796, compound

HRID 2381456Notes

Reaction equation

HRID 2381456 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:13]([OH:15])=O)[C:9](=[O:11])[CH:10]=1.[NH2:30][C:31]1[CH:35]=[CH:34][N:33]([CH2:36][C:37]([CH3:40])([OH:39])[CH3:38])[N:32]=1>>[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:13]([NH:30][C:31]2[CH:35]=[CH:34][N:33]([CH2:36][C:37]([OH:39])([CH3:38])[CH3:40])[N:32]=2)=[O:15])[C:9](=[O:11])[CH:10]=1

Participants

3

Reactant 2

HCID 57919339HCID 57919339, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 44464796HCID 44464796, compoundYield 65%

Procedure

Using the method described in Example 49, 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-(2,6-difluoro-phenyl)-propionic acid (Intermediate 34) 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]-3-(2,6-difluoro-phenyl)-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide as a light yellow solid (571 mg, 65%); ES+-HRMS m/e calcd for C26H23N5O4F4 [M+H+] 546.1759 found 546.1762. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.04 (s, 6H) 3.39-3.58 (m, 2H) 3.88 (s, 2H) 4.66 (s, 1H) 5.70 (dd, J=9.7, 5.6 Hz, 1H) 5.90 (d, J=2.7 Hz, 1H) 6.47 (d, J=2.1 Hz, 1H) 6.96 (t, J=8.0 Hz, 2H) 7.19-7.34 (m, 1H) 7.34-7.41 (m, 2H) 7.42-7.51 (m, 1H) 7.54 (d, J=2.1 Hz, 1H) 8.20 (d, J=2.7 Hz, 1H) 10.67 (s, 1H).

Sources & evidence

ORD record
ord-8af0126f5fa24e8f88b5dd5a37b192aa
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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