3-Iodoaniline → HCID 67501129, compound
Reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH2:10][CH2:9]1)=O)(C)(C)C.I[C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27].[H][H].[F:33][C:34]1[CH:51]=[CH:50][CH:49]=[CH:48][C:35]=1[CH2:36][NH:37][C:38]1[C:43]([C:44]([NH2:46])=[O:45])=[CH:42][N:41]=[C:40](Cl)[CH:39]=1>CCOC(C)=O.[Pd]>[F:33][C:34]1[CH:51]=[CH:50][CH:49]=[CH:48][C:35]=1[CH2:36][NH:37][C:38]1[C:43]([C:44]([NH2:46])=[O:45])=[CH:42][N:41]=[C:40]([NH:27][C:26]2[CH:28]=[CH:29][CH:30]=[C:24]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:25]=2)[CH:39]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The title compound was prepared using similar chemistry as previously described. 4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester was used instead of 3-aminophenylboronic acid and 3-iodoaniline was used instead of 2-bromopyrimidine. 120.1 was then reduced with hydrogen in the presence of Pd/C in EtOAc as seen in scheme BS2. The resulting compound 120.2 was coupled with 4-(2-fluorobenzylamino)-6-chloronicotinamide utilizing chemistry in scheme 1 to afford 120.3. Note that 4-(2-fluorobenzylamino)-6-chloronicotinamide was synthesized analogously to 6-chloro-4-(pyridin-3-ylmethylamino)nicotinamide utilizing 2-fluorobenzylamine instead of 3-(Aminomethyl)pyridine (also see scheme 1). 120.3 was then stirred in a 50/50 mixture of CH2Cl2 and TFA to give the title compound which was purified by rpHPLC (described previously). UV: 257 nm. M+H found for C24H26FN5O: 420.5. (CD3OD): 8.18 (1H, s), 7.414-7.04 (8H, m), 5.94 (1H, s), 4.51 (2H, s), 3.53-3.48 (2H, m), 3.15 (2H, dt, J=2.4 Hz, 8.8 Hz), 2.93 (1H, tt, J=3.6, 8.8 Hz), 2.10-2.06 (2H, m), 1.91 (2H, dd, J=3.6, 12.4 Hz) ppm.
Sources & evidence
- ORD record
- ord-f0d19f3b979a46a5822f9f115490e620
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102625B2
Reaction notes
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