HCID 57919133, compound → HCID 66899380, compound
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][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:13]([OH:15])=O)[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:15])[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][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:37]1)([CH3:31])([CH3:30])[CH3:29]Participants
Procedure
Using the method described in Example 49, 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-(tetrahydro-pyran-4-yl)-propionic acid (Intermediate 32) 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-(tetrahydro-pyran-4-yl)-propionamide as an orange oil (555.9 mg, 47%); ES+-HRMS m/e calcd for C29H39N5O5SiF2 [M+H+] 488.2104 found 488.2103. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.07 (s, 6H) 0.80 (s, 9H) 1.12-1.33 (m, 2H) 1.33-1.45 (m, 1H) 1.46-1.58 (m, 2H) 1.84-1.90 (m, 1H) 1.90 (s, 6H) 2.13-2.25 (m, 1H) 3.10-3.28 (m, 2H) 3.73-3.83 (m, 2H) 3.86 (t, J=5.3 Hz, 2H) 4.06 (t, J=5.3 Hz, 2H) 5.54 (dd, J=10.9, 4.3 Hz, 1H) 6.04 (d, J=2.7 Hz, 1H) 6.36 (d, J=2.1 Hz, 1H) 7.29-7.43 (m, 2H) 7.43-7.52 (m, 1H) 7.53 (d, J=2.1 Hz, 1H) 8.28 (d, J=2.7 Hz, 1H) 10.82 (s, 1H).
Sources & evidence
- ORD record
- ord-07db6413639e4b5f87be50aa8f8ec9e4
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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