Diisobutylaluminumhydride → HCID 17989944, Verbindung

HRID 1292967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292967
C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:35][CH2:34][C:9]2[C:10]3[C:15]([NH:16][C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[N:22]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:21]=[CH:20]5)=[N:14][CH:13]=[N:12][C:11]=3[S:33][C:8]=2[CH2:7]1)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:26]([N:22]1[C:23]2[C:19](=[CH:18][C:17]([NH:16][C:15]3[C:10]4[C:9]5[CH2:34][CH2:35][CH:6]([CH2:5][CH2:4][OH:3])[CH2:7][C:8]=5[S:33][C:11]=4[N:12]=[CH:13][N:14]=3)=[CH:25][CH:24]=2)[CH:20]=[N:21]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 58774537HCID 58774537, Verbindung

Produkt 1

HCID 17989944HCID 17989944, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of THF (100 mL) was added 4.50 g (9.04 mmol, 1 equiv) of [4-(1-Benzyl-1H-indazol-5-ylamino)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-7-yl]-acetic acid ethyl ester. A 1M solution of diisobutylaluminum hydride in THF (45.2 mL, 45.2 mmol, 5 equiv) was added to the solution at 0° C. and the reaction was stirred for 30 min before warming up to rt and stirring for 2 h. The reaction mixture was quenched with Rochelle's salt followed by EtOAc. The solution was separated and the aqueous layer discarded and the organic layer was washed with brine (200 mL) and water (100 mL). The resulting crude material was purified by flash chromatography eluting with 95/5 CH2Cl2/MeOH yielding 850 mg (21%) of Example 203 as a white solid. 1H-NMR (CD2Cl2) δ 8.36 (s, 1H), 8.08 (d, J=1.8 Hz, 1H), 8.01 (s, 1H), 7.46–7.19 (m, 8H), 5.60 (s, 2H), 3.77 (q, J=4.4 Hz, 2H), 3.21–2.96 (m, 3H), 2.56 (m, 1H), 2.11 (m, 2H), 1.67 (m, 3H), 1.45 (t, J=4.4 Hz, 1H). LCMS RT=2.68 min; [M+H]+=456.3.

Aufarbeitung

  1. stirringstirring for 2 h
  2. customThe reaction mixture was quenched with Rochelle's salt
  3. customThe solution was separated
  4. washthe organic layer was washed with brine (200 mL) and water (100 mL)
  5. customThe resulting crude material was purified by flash chromatography
  6. washeluting with 95/5 CH2Cl2/MeOH yielding 850 mg (21%) of Example 203 as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-f0549c75dece41c08f2c39731cef262a
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238701B2

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