Lithium Hydroxide → (E)-4-(8-Morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzoic 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:37]=[CH:36][C:31]([C:32]([O:34]C)=[O:33])=[CH:30][CH:29]=4)=[C:14](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[CH:26][C:25]5[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=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]([C:32]([OH:34])=[O:33])=[CH:36][CH:37]=4)=[C:14](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[CH:26][C:25]5[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=5[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1Participants
3
Procedure
Compound 58d (0.30 g, 0.74 mmol) was hydrolyzed with LiOH using the procedure described in Example 54, Step E to obtain the title compound 76 as a yellow solid. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 13.00 (br, 1H), 8.14-8.11 (m, 3H), 7.81 (d, J=8.1 Hz, 2H), 7.60-7.49 (m, 2H), 7.43 (d, J=8.1 Hz, 1H), 7.33 (d, J=8.1 Hz, 1H), 6.43 (d, J=5.7 Hz, 1H), 4.07-4.02 (m, 4H), 3.85-3.83 (m, 4H), 2.78-2.73 (m, 4H), 1.80-1.75 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H27N5O3: 482.2 (M+H). Found: 482.1.
Sources & evidence
- ORD record
- ord-7f85bf9cd7c04db1a260ec7a5d545cfa
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193736B2
Reaction notes
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