Acetic Anhydride → N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-yl}acetamide

HRID 715612Notes

Reaction equation

HRID 715612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([NH2:23])[CH2:19][CH2:18]1)[N:13]=[CH:12][N:11]=2.[C:37](OC(=O)C)(=[O:39])[CH3:38]>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:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][C:20]([NH:23][C:37](=[O:39])[CH3:38])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]1)[N:13]=[CH:12][N:11]=2

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 714501881-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-amine

Product 1

HCID 89760918N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-yl}acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-amine (6 mg, 0.011 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 6 mg (95%) of desired N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-yl}acetamide. Compound was determined to be 95% pure by 1H NMR. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.95-2.11 (m, 3 H) 2.15-2.39 (m, 2 H) 2.60 (d, J=13.56 Hz, 2 H) 3.69 (br. s., 2 H) 5.23 (br. s., 2 H) 5.71 (br. s., 1 H) 7.10-7.60 (m, 13 H) 8.31-8.48 (m, 1 H), [M−H]− 554.5.

Workup

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

Sources & evidence

ORD record
ord-384c042da4c04c8dbfc153a060e7b5e3
Source dataset
uspto-grants-2015_11
Patent number
US09187480B2

Reaction notes

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