Trifluoroacetic acid → 8-(2-chlorophenyl)-9-(4-chlorophenyl)-N-(piperidin-4-yl)-9H-purin-6-amine

HRID 715615Notes

Reaction equation

HRID 715615 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([NH:17][CH:18]1[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]1)[N:13]=[CH:12][N:11]=2.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=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

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71457343tert-butyl 4-{[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}piperidine-1-carboxylate

Product 1

HCID 714538218-(2-chlorophenyl)-9-(4-chlorophenyl)-N-(piperidin-4-yl)-9H-purin-6-amineYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-{[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}piperidine-1-carboxylate (180 mg, 0.33 mmol) was stirred in dichloromethane (9 mL) and trifluoroacetic acid (4 mL) for 16 h. The reaction was concentrated in vacuo. The crude product was dissolved in ethyl acetate and washed with saturated NaHCO3. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with brine and dried with MgSO4. The crude material was purified by silica gel column chromatography using 0-100% CMA 80/ethyl acetate to yield 129 mg (88%) of 8-(2-chlorophenyl)-9-(4-chlorophenyl)-N-(piperidin-4-yl)-9H-purin-6-amine. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.45 (qd, J=11.66, 3.81 Hz, 2 H) 2.10 (d, J=11.87 Hz, 2 H) 2.64-2.88 (m, 2 H) 3.10 (d, J=12.62 Hz, 2 H) 4.27 (br. s., 1 H) 5.80 (d, J=6.31 Hz, 1 H) 7.01-7.55 (m, 8 H) 8.37 (s, 1 H), [M+H]+ 439.6.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionThe crude product was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried with MgSO4
  7. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e161c044b3994db8b627d4c7d954f9a3
Source dataset
uspto-grants-2015_11
Patent number
US09187480B2

Reaction notes

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