Acetic Anhydride → 1-[(3R)-3-{[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}piperidin-1-yl]ethan-1-one

HRID 715623Notes

Reaction equation

HRID 715623 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][C@@H:18]1[CH2:23][CH2:22][CH2:21][NH: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][C@@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:31](=[O:33])[CH3:32])[CH2:19]1)[N:13]=[CH:12][N:11]=2

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 714573458-(2-chlorophenyl)-9-(4-chlorophenyl)-N-[(3R)-piperidin-3-yl]-9H-purin-6-amine

Product 1

HCID 714591971-[(3R)-3-{[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}piperidin-1-yl]ethan-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 8-(2-chlorophenyl)-9-(4-chlorophenyl)-N-[(3R)-piperidin-3-yl]-9H-purin-6-amine (20 mg, 0.046 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 19 mg (87%) of 1-[(3R)-3-{[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}piperidin-1-yl]ethan-1-one. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.53-1.92 (m, 3 H) 2.07 (br. s., 4 H) 2.84-3.37 (m, 2H) 3.86-4.59 (m, 3 H) 5.88 (br. s., 1 H) 7.04-7.60 (m, 8 H) 8.37 (br. s., 1 H), [M+H]+ 481.3.

Workup

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

Sources & evidence

ORD record
ord-718fab3ad0354f1f991288d850c9ef37
Source dataset
uspto-grants-2015_11
Patent number
US09187480B2

Reaction notes

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