Sodium cyanoborohydride → N4-(1-(2-(1H-Imidazol-1-yl)benzyl)piperidin-4-yl)-N2-(3-(diethylamino)propyl)quinazoline-2,4-diamine
Reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:17]=[C:16]([NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[CH3:2].CN(C)C[CH2:30][CH2:31][NH:32][C:33]1N=[C:41](NC2CCNCC2)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1.N1(C2C=CC=CC=2C=O)C=CN=C1.[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[N:34]1([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=2[CH2:41][N:22]2[CH2:23][CH2:24][CH:19]([NH:18][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]=[C:8]([NH:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:25][CH3:26])[N:17]=3)[CH2:20][CH2:21]2)[CH:30]=[CH:31][N:32]=[CH:33]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 57 mg (0.160 mmol) N2-(3-(diethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine (prepared analogously to Compound 129) and 2-(1H-imidazol-1-yl)benzaldehyde (28 mg, 0.160 mmol) in MeOH (1 ml) was added NaCNBH3 (10 mg, 0.160 mmol) and ZnCl2 (11 mg, 0.08 mmol), The solution was stirred at room temperature overnight. Solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography using 5% NH3 ca. 7 N MeOH in CH2Cl2 and 90% CH2Cl2 solution as eluent to produce the title compound as a brown oil.
Workup
- customSolvent was removed under reduced pressure
- customThe crude product was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-6800b49fd2fd48acb30e628063aa796a
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193203B2
Reaction notes
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