HCID 57919133, compound → HCID 68992089, compound

HRID 2381470Notes

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](O)=[O:14])[C:9](=[O:11])[CH:10]=1.[CH3:28][C:29]1([CH3:41])[O:33][C@H:32]([CH2:34][N:35]2[CH:39]=[CH:38][C:37]([NH2:40])=[N:36]2)[CH2:31][O:30]1>>[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[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[C:13]([NH:40][C:37]2[CH:38]=[CH:39][N:35]([CH2:34][C@@H:32]3[CH2:31][O:30][C:29]([CH3:41])([CH3:28])[O:33]3)[N:36]=2)=[O:14])[C:9](=[O:11])[CH:10]=1

Participants

Reactant 2

HCID 57919133HCID 57919133, compound2×

HCID 59344941(R)-1-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine2×

Product 1

HCID 68992089HCID 68992089, compound

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-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-ylamine (Intermediate 4) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-N-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-3-(tetrahydro-pyran-4-yl)-propionamide as an off-white solid as a mixture of diastereomers (0.60 g, 53%); ES+-HRMS m/e calcd for C27H31N5O6F2 [M+H+] 560.2315 found 560.2319. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13-1.29 (m, 2H), 1.25 (s, 3H), 1.30, 1.31 (2×s, 3H), 1.35-1.59 (m, 3H), 1.84-1.94 (m, 1H), 2.15-2.26 (m, 1H), 3.09-3.27 (m, 2H), 3.70-3.85 (m, 3H), 3.97-4.18 (m, 3H), 4.31-4.40 (m, 1H), 5.54 (dd, J=11.1, 4.0 Hz, 1H), 6.04 (d, J=2.7 Hz, 1H), 6.39 (d, J=2.1 Hz, 1H), 7.34-7.43 (m, 2H), 7.43-7.53 (m, 1H), 7.60 (br s, 1H), 8.29 (d, J=2.7 Hz, 1H), 10.86, 10.87 (2×s, 1H).

Sources & evidence

ORD record: ord-2eb44ee664a14723aa60276df4408cfd
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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