Benzylamine → 4-(5-Aminopyridin-3-yl)-N-benzyl-8-phenylphthalazin-1-amine
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([C:18]2[CH:19]=[C:20]([NH2:24])[CH:21]=[N:22][CH:23]=2)=[N:4][N:3]=1.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(NS(C1C=NC=C(C2C3C(=C(C4C=CC=CC=4)C=CC=3)C(NCC3C=CC=CN=3)=NN=2)C=1)(=O)=O)(C)(C)C>>[NH2:24][C:20]1[CH:19]=[C:18]([C:5]2[C:6]3[C:11](=[C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:9]=[CH:8][CH:7]=3)[C:2]([NH:32][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:3][N:4]=2)[CH:23]=[N:22][CH:21]=1Participants
Procedure
4-(5-Aminopyridin-3-yl)-N-benzyl-8-phenylphthalazin-1-amine (0.300 g, 30.9% yield, white solid) was prepared from 5-(4-chloro-5-phenylphthalazin-1-yl)pyridin-3-amine (0.800 g, 2.40 mmol) and benzylamine (10.0 mL, 92.0 mmol) by the methods described for the preparation of N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide in Example 1. The residue was purified by combiflash (REDISEP®, silica gel, 12 g, 8% MeOH/CHCl3). The resulting residue was further purified by preparative HPLC (Condition 21 as described in general methods). LCMS (Condition 5): retention time 2.03 min, [M+1]=404.6. HPLC (Condition 28): retention time=5.47 min, purity 97.63%. 1H NMR (400 MHz, DMSO-d6) δ 4.49 (d, J=5.2 Hz, 2 H), 4.99 (t, J=5.2 Hz, 1 H), 5.52 (s, 2 H), 7.01-7.03 (m, 2 H), 7.15-7.28 (m, 4 H), 7.43-7.50 (m, 5 H), 7.66 (dd, J=2.0 Hz, J=6.4 Hz, 1 H), 7.85-7.90 (m, 2 H), 7.94 (d, J=2.0 Hz, 1 H), 8.09 (d, J=2.0 Hz, 1 H).
Workup
- customThe residue was purified by combiflash (REDISEP®, silica gel, 12 g, 8% MeOH/CHCl3)
- customThe resulting residue was further purified by preparative HPLC (Condition 21 as described in general methods)
Sources & evidence
- ORD record
- ord-70703b8ecea542399db2cb3a782fc5d8
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242966B2
Reaction notes
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