1,2-Dichloroethane → 4-[4-Chloro-3-(methyloxy)phenyl]-N-(3-ethyl-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734753Notes

Reaction equation

[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH2:12])[CH:10]=2)[NH:5][N:4]=1)[CH3:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][C:24](=[O:26])[NH:23][C:22]([CH3:27])=[C:21]2[C:28](O)=[O:29])=[CH:16][C:15]=1[O:31][CH3:32].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][C:24](=[O:26])[NH:23][C:22]([CH3:27])=[C:21]2[C:28]([NH:12][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][N:4]=[C:3]3[CH2:1][CH3:2])=[O:29])=[CH:16][C:15]=1[O:31][CH3:32]

Participants

Conditions

Temperature: 30 °C

Procedure

3-Ethyl-1H-indazol-5-amine (218 mg, 1.35 mmol, 1.00 equiv) was combined with the product from Example 93, Step 4 (0.400 g, 1.35 mmol, 1.00 equiv), EDC (0.310 g, 1.62 mmol, 1.2 equiv) and Et3N (226 μL, 1.62 mmol, 1.20 equiv) in DMF (4 mL) and stirred at 30° C. for 18 hours. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. Solid precipitated out of the organic phase and was filtered and triturated with ether to provide 295 mg (50%) of the title compound as a white solid. MS (ES+) m/e 439 [M+H]+

Workup

customThe phases were separated
washthe organic phase was washed twice with 1N HCl, once with satd
customSolid precipitated out of the organic phase
filtrationwas filtered
customtriturated with ether

Sources & evidence

ORD record: ord-ae0e4c085be44ad5a6364f88fc28ea08
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592357B2

Reaction notes

Loading…