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Trifluoroacetic acid → 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-amine

HRID 715628
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 715628
[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]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23]C(=O)OC(C)(C)C)[CH2:19][CH2:18]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]([N:17]1[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]1)[N:13]=[CH:12][N:11]=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71459192tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}carbamate

Produkt 1

HCID 715144901-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-amineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}carbamate (380 mg, 0.705 mmol) was stirred in dichloromethane (7 mL) and trifluoroacetic acid (3 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 294 mg (95%) of 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-amine. Compound was determined to be 95% pure by 1H NMR and was carried forward into further chemistry. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.31-1.54 (m, 2 H) 1.92-2.08 (m, 2 H) 2.92-3.12 (m, 1 H) 3.27 (t, J=11.87 Hz, 2 H) 5.42 (br. s., 2 H) 7.07-7.61 (m, 8 H) 8.38 (s, 1 H), [M+H]+ 439.4.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a295faeaeb7c4aafbc80243dc87e5d88
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09187480B2

Notizen zur Reaktion

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