Trifluoroacetic acid → 5-amino-2-[2-(4-fluorophenyl)ethyl]-7-(1-(4-chlorophenoxyacetyl)pyrrolidin-3-(S)-ylamino)-thiazolo[5,4-d]pyrimidine

HRID 1507809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1507809
[NH2:1][C:2]1[N:3]=[C:4]([NH:20][C@H:21]2[CH2:25][CH2:24][N:23]([C:26](OC(C)(C)C)=[O:27])[CH2:22]2)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[S:8][C:6]=2[N:7]=1.FC(F)(F)C(O)=O.C(N(C(C)C)CC)(C)C.[Cl:49][C:50]1[CH:60]=[CH:59][C:53]([O:54][CH2:55]C(Cl)=O)=[CH:52][CH:51]=1>ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([NH:20][C@H:21]2[CH2:25][CH2:24][N:23]([C:26](=[O:27])[CH2:55][O:54][C:53]3[CH:59]=[CH:60][C:50]([Cl:49])=[CH:51][CH:52]=3)[CH2:22]2)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=3)[S:8][C:6]=2[N:7]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 77771p-Chlorophenoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 469168485-amino-2-[2-(4-fluorophenyl)ethyl]-7-(1-tert-butoxycarbonyl-pyrrolidin-3-(S)-ylamino)-thiazolo[5,4-d]pyrimidine

Produkt 1

HCID 469168495-amino-2-[2-(4-fluorophenyl)ethyl]-7-(1-(4-chlorophenoxyacetyl)pyrrolidin-3-(S)-ylamino)-thiazolo[5,4-d]pyrimidineAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-2-[2-(4-fluorophenyl)ethyl]-7-(1-tert-butoxycarbonyl-pyrrolidin-3-(S)-ylamino)-thiazolo[5,4-d]pyrimidine (70 mg, 0.15 mmol) in dichloromethane (1 ml) was added trifluoroacetic acid (1 ml). The reaction mixture was stirred at room temperature for 2 hours after which the solvents were removed in vacuo. The residue was dissolved in dichloromethane (3 ml) and diisopropylethylamine (1.5 mmol, 252 μL) and 4-chlorophenoxyacetyl chloride (0.17 mmol) were added. The reaction mixture was stirred at room temperature for 16 hours whereupon the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 1.5% CH3OH in CH2Cl2), yielding the pure title compound (37 mg) which was characterized by its mass spectrum: MS m/z (%): 527 ([M+H]+, 100).

Aufarbeitung

  1. customwere removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (3 ml)
  3. stirringThe reaction mixture was stirred at room temperature for 16 hours whereupon the solvent
  4. customwas removed in vacuo
  5. customThe resulting residue was purified by flash chromatography on silica
  6. additiona mixture of methanol and dichloromethane (in a ratio

Quellen und Nachweise

ORD-Eintrag
ord-80871a9ee02f48b0950486f355c1e97e
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221822B2

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