4-(N-Boc-amino)piperidine → tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}carbamate

HRID 715627Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[NH:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:27][CH2:26]1>C(O)C>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:5]1[N:6]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:7]2[C:3]([N:4]=1)=[C:2]([N:25]1[CH2:26][CH2:27][CH:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:29][CH2:30]1)[N:10]=[CH:9][N:8]=2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purine (309 mg, 0.824 mmol, 1 eq.) in 10 mL of ethanol was added tert-butyl N-(piperidin-4-yl)carbamate (329 mg, 1.65 mmol, 2 eq.). The reaction was heated to 80° C. 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 442 mg (99%) of tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}carbamate. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.40-1.53 (m, 11 H) 2.12 (d, J=11.40 Hz, 2 H) 3.32 (t, J=11.63 Hz, 2 H) 3.80 (br. s., 1 H) 4.41-4.68 (m, 1 H) 5.40 (br. s., 2 H) 7.16-7.24 (m, 2 H) 7.26-7.43 (m, 5 H) 7.51 (d, J=6.59 Hz, 1 H) 8.38 (s, 1 H), [M+H]+ 539.2.

Workup

concentrationThe reaction was concentrated in vacuo
customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-d010bf804ceb4149ba3360e49dafe406
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187480B2

Reaction notes

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