HCID 178471560, Verbindung → HCID 178471572, Verbindung

HRID 1639244

Reaktionsgleichung

Reaktionsgleichung von HRID 1639244
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]([C:29]1[CH:50]=[CH:49][C:32]([C:33]([NH:35][C@H:36]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:34])=[CH:31][CH:30]=1)=[CH:10][C:11]1[CH:28]=[N:27][C:14]2[N:15]=[C:16]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[N:17]=[C:18]([OH:19])[C:13]=2[CH:12]=1>C(O)(=O)C.CO.[Pt](=O)=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]([C:29]1[CH:50]=[CH:49][C:32]([C:33]([NH:35][C@H:36]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:34])=[CH:31][CH:30]=1)[CH2:10][CH:11]1[CH2:28][NH:27][C:14]2[N:15]=[C:16]([NH:20][C:21](=[O:26])[C:22]([CH3:23])([CH3:25])[CH3:24])[N:17]=[C:18]([OH:19])[C:13]=2[CH2:12]1

Komponenten

5

Edukt 1

HCID 178471560HCID 178471560, Verbindung

Produkt 1

HCID 178471572HCID 178471572, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 345198Adams' catalystKatalysatorHCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1.16 g (1.68 mm) of diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)prop-2-en-2-yl}benzoyl]glutamate and 174 mg (20%) of amorphous platinum (IV) oxide in 150 ml of glacial acetic acid was hydrogenated for 10 hours at 50 psi. The reaction mixture was diluted with 50 ml of methanol and filtered through Celite. The filtrate was concentrated and diluted with ethyl acetate. The solid which formed after cooling for 15 hour was collected by filtration, washed with cold ethyl acetate and dried to give 700 mg (68%) of diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl}benzoyl]glutamate. mp 183°-186° C. Analysis calculated for C36H51O9N5 : C, 61.95; H, 7.37; N, 10.04. Found: C, 62.00; H, 7.17; N, 9.83. NMR (CDCL3), delta, 1.23 (t, 3H, J=7 Hz), 1.26 (s, 9H), 1.32 (t, 3H, J=7 Hz), 2.26-2.82 (m, 9H), 2.06-2.12 (m, 2H), 2.26-2.38 (m, 1H), 2.43-2.58 (m, 2H), 2.62-2.83 (m, 1H), 2.84-3.10 (m, 2H) 3.12-3.21 and 2.32-3.40 (m, m, 1H), 3.41-3.52 (m, 2H), 3.68-3.92 (m, 2H), 4.13 (q, 2H, J=7 Hz), 4.25 (q, 2H, J=7 Hz), 4.44-4.63 (m, 2H, CH, NH), 4.78-4.84 (m, 1H) 7.02 (brd, 1H, NH, J=7.1 Hz), 7.29 (brs, NH), 7.31-7.37 (m, 2H), 7.75-7.78 (m, 2H), 11.20 (brs, NH).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with ethyl acetate
  4. customThe solid which formed
  5. temperatureafter cooling for 15 hour
  6. filtrationwas collected by filtration
  7. washwashed with cold ethyl acetate
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0d57ad2024c645e88bc41651ef1ffa03
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04883799

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