HCID 57919097, compound → HCID 66898792, compound
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.[C:25]([Si:29]([CH3:40])([CH3:39])[O:30][CH2:31][CH2:32][N:33]1[CH:37]=[CH:36][C:35]([NH2:38])=[N:34]1)([CH3:28])([CH3:27])[CH3:26]>>[C:25]([Si:29]([CH3:40])([CH3:39])[O:30][CH2:31][CH2:32][N:33]1[CH:37]=[CH:36][C:35]([NH:38][C:13](=[O:15])[CH:12]([N:8]2[C:9](=[O:11])[CH:10]=[C:5]([O:4][C:3]3[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:2]=3[F:1])[CH:6]=[N:7]2)[CH2:16][CH:17]([CH3:19])[CH3:18])=[N:34]1)([CH3:28])([CH3:27])[CH3:26]Participants
Procedure
Using the method described in Example 49, 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-methyl-pentanoic acid (Intermediate 28) and 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine (Intermediate 3) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-methyl-pentanoic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-yl}-amide as an off-white solid (1.15 g, 68%); ES+-HRMS m/e calcd for C27H37N5O4SiF2 [M+H+] 562.2656 found 562.2658. 1H NMR (300 MHz, DMSO-d6) δ ppm −0.06 (s, 6H) 0.81 (s, 9H) 0.84-0.92 (m, 6H) 1.45 (m, 1H) 1.70-1.87 (m, 1H) 2.09-2.24 (m, 1H) 3.86 (t, J=5.1 Hz, 2H) 4.07 (t, J=5.1 Hz, 2H) 5.53 (dd, J=11.2, 4.2 Hz, 1H) 6.04 (d, J=2.7 Hz, 1H) 6.36 (d, J=2.0 Hz, 1H) 7.31-7.52 (m, 3H) 7.54 (d, J=2.0 Hz, 1H) 8.28 (d, J=2.7 Hz, 1H) 10.82 (s, 1H).
Sources & evidence
- ORD record
- ord-72816349cac9419280ae25e9c3676e51
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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