HCID 57919339, compound → HCID 68995070, compound

HRID 2381464Notes

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](O)=[O:14])[C:9](=[O:11])[CH:10]=1.[C:30]([Si:34]([CH3:45])([CH3:44])[O:35][CH2:36][CH2:37][N:38]1[CH:42]=[CH:41][C:40]([NH2:43])=[N:39]1)([CH3:33])([CH3:32])[CH3:31]>>[C:30]([Si:34]([CH3:45])([CH3:44])[O:35][CH2:36][CH2:37][N:38]1[CH:42]=[CH:41][C:40]([NH:43][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:28][CH:27]=[CH:26][C:25]=3[F:29])[CH:6]=[N:7]2)[CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])=[N:39]1)([CH3:33])([CH3:32])[CH3:31]

Participants

Reactant 2

HCID 57919339HCID 57919339, compound2×

HCID 593449471-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine2×

Product 1

HCID 68995070HCID 68995070, 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-[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-(2,6-difluoro-phenyl)-propionamide as a light yellow solid (690 mg, 65%); ES+-HRMS m/e calcd for C30H33N5O4SiF4 [M+H+] 632.2311 found 632.2311. 1H NMR (300 MHz, DMSO-d6) δ ppm −0.08 (s, 6H) 0.80 (s, 9H) 3.24-3.34 (m, 1H) 3.49 (dd, J=14.5, 5.7 Hz, 1H) 3.83 (t, J=5.1 Hz, 2H) 4.00-4.10 (m, 2H) 5.69 (dd, J=9.8, 5.6 Hz, 1H) 5.89 (d, J=2.7 Hz, 1H) 6.43 (d, J=2.1 Hz, 1H) 6.96 (t, J=8.0 Hz, 2H) 7.18-7.52 (m, 4H) 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-c4f1aad5d1964103aa04967a8629b659
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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