(6-Bromo-4-(6-(2-(dimethylamino)ethylamino)pyridine-3-ylamino)quinolin-3-yl)(cyclopropyl)methanone → (6-(3-Chloro-5-fluoro-4-hydroxyphenyl)-4-(6-(2-(dimethylamino)ethylamino)pyridin-3-ylamino)quinolin-3-yl)(cyclopropyl)methanone
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][C:18]1[CH:19]=[N:20][C:21]([NH:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])=[CH:22][CH:23]=1.[Cl:30][C:31]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=[C:33]([F:46])[C:32]=1[OH:47]>>[Cl:30][C:31]1[CH:36]=[C:35]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[C:5]3[NH:17][C:18]2[CH:19]=[N:20][C:21]([NH:24][CH2:25][CH2:26][N:27]([CH3:28])[CH3:29])=[CH:22][CH:23]=2)[CH:34]=[C:33]([F:46])[C:32]=1[OH:47]Participants
3
Reactant 2
Product 1
Procedure
Following general procedure D, (6-bromo-4-(6-(2-(dimethylamino)ethylamino)pyridin-3-ylamino)quinolin-3-yl)(cyclopropyl)methanone (75 mg, 0.17 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (69 mg, 0.25 mmol) to afford the desired product (6 mg, 7%) as a yellow-orange solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.40 (s, 1H), 8.25 (dd, J=8.8, 1.9 Hz, 1H), 8.22-8.15 (m, 2H), 8.03 (d, J=8.8 Hz, 1H), 7.69 (dd, J=9.1, 2.6 Hz, 1H), 7.27-7.18 (m, 2H), 6.95 (d, J=9.1 Hz, 1H), 3.87-3.81 (m, 2H), 3.46-3.39 (m, 2H), 2.97 (s, 6H), 2.89-2.78 (m, 1H), 1.28-1.17 (m, 4H); ESI MS m/z 520 [C28H27ClFN5O2+H]+; HPLC>99% (AUC), tR=10.34 min.
Sources & evidence
- ORD record
- ord-53056a7942bf4200bf9be53217541d83
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120749B2
Reaction notes
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