Acetic Anhydride → 1(4-{[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}piperidin-1-yl)ethan-1-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([NH:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[N:13]=[CH:12][N:11]=2.[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([NH:17][CH:18]1[CH2:23][CH2:22][N:21]([C:31](=[O:33])[CH3:32])[CH2:20][CH2:19]1)[N:13]=[CH:12][N:11]=2Participants
Procedure
A solution of 8-(2-chlorophenyl)-9-(4-chlorophenyl)-N-(piperidin-4-yl)-9H-purin-6-amine (19.3 mg, 0.044 mmol, 1 eq.) in 1 mL of acetic anhydride and 1 mL of pyridine was stirred for 16 h. The reaction was concentrated in vacuo. The crude material was purified by silica gel column chromatography using 0-100% ethyl acetate/hexanes to yield 9 mg (43%) of desired 1(4-{[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}piperidin-1-yl)ethan-1-one. Compound was determined to be 95% pure by 1H NMR. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.36-1.52 (m, 2 H) 2.03-2.27 (m, 5 H) 2.81 (t, J=11.49 Hz, 1 H) 3.13-3.33 (m, 1 H) 3.81 (d, J=13.75 Hz, 1 H) 4.41 (br. s., 1 H) 4.55 (d, J=13.66 Hz, 1H) 5.78 (br. s., 1 H) 7.00-7.55 (m, 8 H) 8.37 (s, 1 H), [M+Na]+ 503.8.
Workup
- concentrationThe reaction was concentrated in vacuo
- customThe crude material was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-2925879bedf64d19b479ca545ad4ef76
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187480B2
Reaction notes
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