2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-phenyl-propionic acid → N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-yl}-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-phenyl-propionamide
Reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13](O)=[O:14])[C:9](=[O:11])[CH:10]=1.[C:28]([Si:32]([CH3:43])([CH3:42])[O:33][CH2:34][CH2:35][N:36]1[CH:40]=[CH:39][C:38]([NH2:41])=[N:37]1)([CH3:31])([CH3:30])[CH3:29]>>[C:28]([Si:32]([CH3:43])([CH3:42])[O:33][CH2:34][CH2:35][N:36]1[CH:40]=[CH:39][C:38]([NH:41][C:13](=[O:14])[CH:12]([N:8]2[C:9](=[O:11])[CH:10]=[C:5]([O:4][C:3]3[C:2]([F:1])=[CH:26][CH:25]=[CH:24][C:23]=3[F:27])[CH:6]=[N:7]2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:37]1)([CH3:31])([CH3:30])[CH3:29]Participants
Reactant 2
Product 1
Procedure
Using the method described in Example 49, 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-phenyl-propionic acid (Intermediate 30) and 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine (Intermediate 3) afforded N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-yl}-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-phenyl-propionamide as a light yellow solid (1.07 g, 57%); ES+-HRMS m/e calcd for C30H35N5O4SiF2 [M+H+] 596.2499 found 596.2499. 1H NMR (300 MHz, DMSO-d6) δ ppm −0.06 (s, 6H) 0.80 (s, 9H) 3.36-3.50 (m, 2H) 3.86 (t, J=5.1 Hz, 2H) 4.08 (t, J=5.1 Hz, 2H) 5.75-5.88 (m, 1H) 5.93 (d, J=2.7 Hz, 1H) 6.40 (d, J=2.1 Hz, 1H) 7.06-7.53 (m, 8H) 7.56 (d, J=2.1 Hz, 1H) 8.25 (d, J=2.7 Hz, 1H) 10.99 (s, 1H).
Sources & evidence
- ORD record
- ord-62bf88ce5fa149079f48f18bc14e9284
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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