2-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid → HCID 59304200, compound
Reaction equation
[NH2:1][C:2]1[CH:40]=[CH:39][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[N:13](CC4C=CC(OC)=CC=4)[N:14]=[C:15]([NH:16][CH:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)[C:8]=23)=[C:4]([F:41])[CH:3]=1.[F:42][C:43]1[CH:48]=[CH:47][C:46]([N:49]2[C:54](=[O:55])[C:53]([C:56]([OH:58])=O)=[CH:52][CH:51]=[N:50]2)=[CH:45][CH:44]=1>>[F:41][C:4]1[CH:3]=[C:2]([NH:1][C:56]([C:53]2[C:54](=[O:55])[N:49]([C:46]3[CH:45]=[CH:44][C:43]([F:42])=[CH:48][CH:47]=3)[N:50]=[CH:51][CH:52]=2)=[O:58])[CH:40]=[CH:39][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:13][N:14]=[C:15]([NH:16][CH:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)[C:8]=12Participants
Procedure
Prepared by a 2-step process from tert-butyl 4-(4-(4-amino-2-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-ylamino)piperidine-1-carboxylate (prepared as described in Example 101, Step A, using tert-butyl 4-aminopiperidine-1-carboxylate) and 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid according to the procedure of Example 101, Step B. The crude material was purified by silica gel flash column chromatography (60% MeOH in CH2Cl2) to afford 19 mg (34%) of the desired product. LRMS (ESI pos) m/e 559.1 (M+1). 1H-NMR (400 MHz, CD3OD/CDCl3) δ 8.41 (d, 1H), 8.33 (d, 1H), 8.14 (d, 1H), 8.02 (dd, 1H), 7.65 (m, 2H), 7.47 (d, 1H), 7.37 (t, 1H), 7.28 (t, 2H), 6.12 (d, 1H), 3.80 (m, 1H), 3.16 (d, 2H), 2.79 (t, 2H), 2.24 (d, 2H), 1.53 (m, 2H); 19F NMR (376 MHz, CD3OD/CDCl3) δ −113.1, −127.7.
Workup
- customThe crude material was purified by silica gel flash column chromatography (60% MeOH in CH2Cl2)
Sources & evidence
- ORD record
- ord-34d52f5cd29f4c7cb6b5a8b4714ac5d6
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723330B2
Reaction notes
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