1-Methylpyrrolidine → N-(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide
Reaction equation
[C:1]([NH:7][C:8](=[O:30])[NH:9][C:10]1[N:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:29])OC(C)=C)[CH:18]=2)=[CH:12][CH:11]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.CN1CCCC1>O1CCOCC1>[C:1]([NH:7][C:8](=[O:30])[NH:9][C:10]1[N:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:29])[CH:18]=2)=[CH:12][CH:11]=1)(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of Example C2 (0.163 g, 0.394 mmol), pyrrolidine (0.028 g, 0.394 mmol) and N-methylpyrrolidine (0.017 g, 0.197 mmol) in dioxane (3 mL) was heated at 80° C. for 45 min, cooled to RT, and concentrated to dryness. The residue was suspended in MeCN and the mixture was sonicated for a few minutes. The light beige solid was collected by filtration, washed with MeCN and dried overnight at 80° C. to provide N-(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide (0.118 g, 67%). 1H NMR (400 MHz, DMSO-d6): δ 11.22 (s, 1H), 10.44 (s, 1H), 8.72 (s, 1H), 8.23 (d, J=2.9 Hz, 1H), 8.13-8.04 (m, 2H), 7.71 (dd, J=9.0, 2.9 Hz, 1H), 7.47 (d, J=2.4 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 3.39-3.30 (m, 4H), 1.84-1.71 (m, 4H), 1.21 (s, 9H); MS (ESI) m/z: 427.2 (M+H+).
Workup
- concentrationconcentrated to dryness
- customthe mixture was sonicated for a few minutes
- filtrationThe light beige solid was collected by filtration
- washwashed with MeCN
- customdried overnight at 80° C.
Sources & evidence
- ORD record
- ord-69e36d21816749a39386ad3cf0d724c2
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309224B2
Reaction notes
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