HCID 54762049, compound → HCID 86702369, compound
Reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:40])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:39])[C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]4[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH2:29]4)=[CH:23][N:22]=3)=[CH:15][CH:14]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1[O:49]N=C(NC(=O)NC2C=CC(NC(=O)C3C=CC(OC4CCN(C(C)C)CC4)=CN=3)=CC=2)C=1)(C)(C)C>>[CH3:38][S:35]([O-:36])(=[O:37])=[O:49].[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:40])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:21]3[N:22]=[CH:23][C:24]([O:27][CH:28]4[CH2:32][CH2:31][NH+:30]([CH2:33][CH2:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH2:29]4)=[CH:25][CH:26]=3)=[O:39])=[CH:15][CH:14]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
3-(6-(4-(3-(5-tert-Butylisoxazol-3-yl)ureido)phenylcarbamoyl)pyridin-3-yloxy)-1-(2-(methylsulfonyl)ethyl)pyrrolidinium methanesulfonate (150 mg, 95%) was prepared using a procedure analogous to that described in Example 27, substituting N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)-5-(1-(2-(methylsulfonyl)ethyl)pyrrolidin-3-yloxy)picolinamide from Step 1 of this example for N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)-5-(1-isopropylpiperidin-4-yloxy)picolinamide used in Step 2 of Example 27. LC-MS (ESI) m/z 571 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 10.41 (s, 1H), 9.51 (s, 1H), 8.83 (s, 1H), 8.39 (br. s., 1H), 8.14 (d, J=8.67 Hz, 1H), 7.81 (d, J=8.29 Hz, 2H), 7.67 (d, J=8.29 Hz, 1H), 7.43 (d, J=8.48 Hz, 2H), 6.50 (s, 1H), 5.39 (br. s., 1H), 3.66 (br. s., 7H), 3.12 (s, 3H), 2.70 (d, J=16.39 Hz, 1H), 2.42-2.29 (overlapping m, 1H), 2.35 (s, 3H), 2.15 (d, J=10.17 Hz, 1H), 1.30 (s, 9H).
Sources & evidence
- ORD record
- ord-3384f955cc344db1871771b4c149c6ee
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296722B2
Reaction notes
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