Lithium Hydroxide → (E)-3-(5-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)propanoic acid
Reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])=[N:32][CH:33]=4)=[C:14](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[Li+].[OH-]>>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[N:32][CH:33]=4)=[C:14](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1Participants
3
Procedure
Compound 57d (0.58 g, 1.1 mmol) was hydrolyzed with LiOH using the procedure described in Example 54, Step E. The title compound 125 was obtained as a yellow solid. 1H-NMR (300 MHz, CD3OD) δ (ppm): 8.81 (d, J=1.5 Hz, 1H), 8.30 (d, J=8.4 Hz, 1H), 8.16 (dd, J=8.1, 2.1 Hz, 1H), 8.09 (d, J=5.7 Hz, 1H), 8.00 (t, J=8.4 Hz, 1H), 7.92-7.87 (m, 3H), 7.80-7.73 (m, 2H), 7.63-7.54 (m, 2H), 6.40 (d, J=5.7 Hz, 1H), 4.13-4.10 (m, 4H), 4.00-3.97 (m, 4H), 3.23 (t, J=7.5 Hz, 2H), 2.71 (t, J=7.5 Hz, 2H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C29H26N6O3: 507.2 (M+H). Found: 507.1.
Sources & evidence
- ORD record
- ord-a7edae01c3de487eb2944ab521ef576d
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193736B2
Reaction notes
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