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3-[3-({[(3aR,4R,6R,6aR)-6-(6-Amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl}(methyl)amino)cyclobutyl]-N-[2-amino-4-(1-methoxy-2-methylpropan-2-yl)phenyl]propanamide → HCID 178494914, Verbindung

HRID 511683
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 511683
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][N:22]([CH3:45])[CH:23]2[CH2:26][CH:25]([CH2:27][CH2:28][C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([CH3:43])([CH3:42])[CH2:39][O:40][CH3:41])=[CH:34][C:33]=3[NH2:44])=O)[CH2:24]2)[O:12]1>CC(O)=O>[CH3:41][O:40][CH2:39][C:38]([C:35]1[CH:36]=[CH:37][C:32]2[NH:31][C:29]([CH2:28][CH2:27][CH:25]3[CH2:24][CH:23]([N:22]([CH2:21][C@@H:13]4[C@H:14]5[O:18][C:17]([CH3:19])([CH3:20])[O:16][C@H:15]5[C@H:11]([N:6]5[CH:5]=[N:4][C:3]6[C:7]5=[N:8][CH:9]=[N:10][C:2]=6[NH2:1])[O:12]4)[CH3:45])[CH2:26]3)=[N:44][C:33]=2[CH:34]=1)([CH3:42])[CH3:43]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

3

Edukt 1

HCID 677750013-[3-({[(3aR,4R,6R,6aR)-6-(6-Amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl}(methyl)amino)cyclobutyl]-N-[2-amino-4-(1-methoxy-2-methylpropan-2-yl)phenyl]propanamide

Produkt 1

HCID 178494914HCID 178494914, VerbindungAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3-[3-({[(3aR,4R,6R,6aR)-6-(6-Amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl}(methyl)amino)cyclobutyl]-N-[2-amino-4-(1-methoxy-2-methylpropan-2-yl)phenyl]propanamide (1.036 g, 1.66 mmol) was dissolved in AcOH (17 ml) and heated to 50° C. for 5 h. The reaction was concentrated in vacuo and the residue was dissolved in DCM (75 ml) and sat. NaHCO3 solution (75 ml) was added. The organic layer was separated and the aqueous layer was extracted with DCM (2×75 ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product as a dark orange oil (0.850 g, 94%). The product was purified using neutral prep-HPLC to give the product as a pale yellow oil (0.485 g, 47%, 88% pure): MS (ESI+) for C32H44N8O4 m/z 605.4 [M+H]+; LC purity 88% (ret. time, 1.25 min); 1H NMR (500 MHz, CDCl3) δH 10.44 (dd, J=207.7, 22.9 Hz, 1H), 8.41 (d, J=17.1 Hz, 1H), 8.16 (d, J=13.8 Hz, 1H), 7.89-7.58 (m, 1H), 7.54-7.29 (m, 2H), 6.15 (d, J=10.9 Hz, 1H), 5.92-5.56 (m, 3H), 4.98 (d, J=12.5 Hz, 1H), 4.76-4.39 (m, 1H), 3.47 (d, J=6.2 Hz, 2H), 3.33 (d, J=4.8 Hz, 3H), 2.98-2.43 (m, 4H), 2.42-2.00 (m, 6H), 1.99-1.88 (m, 2H), 1.77-1.66 (m, 1H), 1.64 (s, 3H), 1.61-1.48 (m, 1H), 1.44 (d, J=8.1 Hz, 3H), 1.40 (d, J=7.9 Hz, 6H), 1.28 (dd, J=16.0, 9.0 Hz, 1H).

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in DCM (75 ml)
  3. additionsat. NaHCO3 solution (75 ml) was added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with DCM (2×75 ml)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude product as a dark orange oil (0.850 g, 94%)
  10. customThe product was purified

Quellen und Nachweise

ORD-Eintrag
ord-6cc66f72a26b4a5f868cc80d1f24d187
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096634B2

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