Triethylamine → tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-yl}carbamate

HRID 715609Notes

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.[C:25]1([C:31]2([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>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:34]1[CH2:33][CH2:32][C:31]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:41])[CH3:43])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:36][CH2:35]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 (50 mg, 0.133 mmol, 1 eq.) in 2 mL of ethanol was added tert-butyl N-(4-phenylpiperidin-4-yl)carbamate (44 mg, 0.16 mmol, 1.2 eq) and triethylamine (0.03 mL, 0.20 mmol, 1.5 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 69 mg (84%) of tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-yl}carbamate. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.31-1.49 (m, 9H) 2.09-2.28 (m, 2 H) 2.43 (br. s., 2 H) 3.62 (br. s., 2 H) 4.96 (s, 1 H) 5.30 (br. s., 2H) 7.03-7.61 (m, 13H) 8.40 (s, 1 H), [M+H]+ 615.4.

Workup

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

Sources & evidence

ORD record: ord-5d74bebc9f844c9ca3c220747eb9bcbf
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187480B2

Reaction notes

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