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Hydrochloric Acid → HCID 178457040, Verbindung

HRID 2040675
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2040675
[C:1]([C:5]1[CH:52]=[CH:51][C:8]2[N:9](COCC[Si](C)(C)C)[C:10]([CH2:12][CH:13]3[CH2:16][CH:15]([CH2:17][N:18]([CH2:22][C@@H:23]4[C@H:27]5[O:28]C(C)(C)[O:30][C@H:26]5[C@H:25]([N:33]5[C:37]6[N:38]=[CH:39][N:40]=[C:41]([NH2:42])[C:36]=6[CH:35]=[CH:34]5)[CH2:24]4)[CH:19]([CH3:21])[CH3:20])[CH2:14]3)=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>CO>[NH2:42][C:41]1[C:36]2[CH:35]=[CH:34][N:33]([C@@H:25]3[CH2:24][C@H:23]([CH2:22][N:18]([CH2:17][CH:15]4[CH2:14][CH:13]([CH2:12][C:10]5[NH:9][C:8]6[CH:51]=[CH:52][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=6[N:11]=5)[CH2:16]4)[CH:19]([CH3:20])[CH3:21])[C@@H:27]([OH:28])[C@H:26]3[OH:30])[C:37]=2[N:38]=[CH:39][N:40]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 677748577-[(3aS,4R,6R,6aR)-6-{[({3-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutyl}methyl)(propan-2-yl)amino]methyl}-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Produkt 1

HCID 178457040HCID 178457040, VerbindungAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

7-[(3aS,4R,6R,6aR)-6-{[({3-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutyl}methyl)(propan-2-yl)amino]methyl}-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (58.7 mg, 0.08 mmol) was dissolved in cone. HCl solution (5 ml) and methanol (5 ml) and heated to 40° C. for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue partitioned between sat. NaHCO3(aq) (10 ml) and EtOAc (10 ml). The layers were separated and the aqueous layer was extracted with EtOAc (2×10 ml), the combined organics were then dried (MgSO4) and concentrated. The crude material was purified by prep TLC, eluting with 10% 2M NH3 in MeOH in DCM to afford the title compound (24.7 mg, 55%) as a colourless gum: MS (ESI+) for C32H45N7O2 m/z 560.4 [M+H]+; LC purity 100% (UV), (ret. time, 5.10 min); 1H NMR (500 MHz, Acetone) δH 8.12 (s, 1 H), 7.30-7.60 (m, 2 H), 7.13-7.28 (m, 2 H), 6.54 (d, J=3.5 Hz, 1 H), 6.33 (br. s., 1 H), 4.85-5.07 (m, 1 H), 4.36 (t, J=6.2 Hz, 1 H), 4.08 (t, J=5.2 Hz, 1 H), 3.01 (d, J=7.7 Hz, 1 H), 2.93 (d, J=7.4 Hz, 2 H), 2.78 (br. s., 2 H), 2.59-2.73 (m, 2 H), 2.15-2.56 (m, 7 H), 1.68 (dt, J=12.4, 9.7 Hz, 1 H), 1.44-1.62 (m, 2 H), 1.35 (s, 9 H), 0.90-1.07 (m, 6 H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between sat. NaHCO3(aq) (10 ml) and EtOAc (10 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×10 ml)
  5. dry with materialthe combined organics were then dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by prep TLC
  8. washeluting with 10% 2M NH3 in MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-d053d428858a4848be5f50ddac97a710
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08580762B2

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