Pyridine → N-(5-(4-(benzylamino)-5-phenylphthalazin-1-yl)pyridin-3-yl)acetamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=[CH:15][CH:16]=3)[C:11]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:10][N:9]=2)[CH:5]=[N:6][CH:7]=1.N1C=CC=CC=1.[C:38](Cl)(=[O:40])[CH3:39]>C(Cl)Cl>[CH2:25]([NH:24][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:38](=[O:40])[CH3:39])[CH:7]=[N:6][CH:5]=2)=[N:9][N:10]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Participants
Procedure
To a solution of 4-(5-aminopyridin-3-yl)-N-benzyl-8-phenylphthalazin-1-amine (60.0 mg, 0.149 mmol) in DCM (20 mL) was added pyridine (0.0241 mL, 0.297 mmol) at room temperature followed by acetyl chloride (0.0106 mL, 0.149 mmol) and stirred at the same temperature for 5 h. The volatile components were removed under reduced pressure and the resulting residue was purified by preparative HPLC (Condition 19 as described in general methods) to yield N-(5-(4-(benzylamino)-5-phenylphthalazin-1-yl)pyridin-3-yl)acetamide (45.0 mg, 67.9%) as a white solid. LCMS (Condition 4): retention time 2.44 min, [M+1]=446.2. HPLC (Condition 28): retention time=6.44 min, purity 97.94%. 1H NMR (400 MHz, DMSO-d6) δ 2.13 (s, 3 H), 4.51 (d, J=4.8 Hz, 2 H), 5.06 (dd, J=4.8 Hz, J=5.2 Hz, 1 H), 7.02-7.04 (m, 2 H), 7.23-7.29 (m, 3 H), 7.42-7.52 (m, 5 H), 7.68 (dd, J=1.6 Hz, J=7.2 Hz, 1 H), 7.85-7.93 (m, 2 H), 8.36 (dd, J=2.0 Hz, J=2.4 Hz, 1 H), 8.52 (d, J=2.0 Hz, 1 H), 8.84 (d, J=2.0 Hz, 1 H), 10.37 (s, 1 H).
Workup
- customThe volatile components were removed under reduced pressure
- customthe resulting residue was purified by preparative HPLC (Condition 19 as described in general methods)
Sources & evidence
- ORD record
- ord-7cbea2f65fe84c2493d46270e67e1b19
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242966B2
Reaction notes
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