Hydrochloric Acid → HCID 19756360, Verbindung

HRID 1587835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587835
Cl.[CH2:2]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:29]=[N:30][N:31]([C:33]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:32]=3)=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:52][CH2:53][CH:54]=[O:55])[N:10]=2)[N:5]=1)[CH3:3].N1CC[O:59][CH2:58][CH2:57]1.C([BH3-])#N.[Na+]>C(O)C.CO>[CH2:2]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:29]=[N:30][N:31]([C:33]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:32]=3)=[CH:20][CH:21]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:52][CH2:53][C:54]([O:59][CH2:58][CH3:57])=[O:55])[N:10]=2)[N:5]=1)[CH3:3]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 19756390HCID 19756390, Verbindung

Produkt 1

HCID 19756360HCID 19756360, VerbindungAusbeute 23,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A saturated solution of hydrogen chloride in ethanol (0.1 ml) was added to a solution of compound B (600 mg) and morpholine (450 mg) in methanol (10 ml) containing 3A molecular sieves (1 g). Sodium cyanoborohydride (53 mg) was added and the mixture was stirred for 20 hours. Volatile material was removed by evaporation and the residue purified by flash chromatography, eluting with methanol/ethyl acetate (1:9 v/v). to give 2-ethyl-6-[2-(4-morpholino)ethoxy]-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A) (152 mg), m.p. 135°-137° C. (after trituration with hexane); NMR (d6 -DMSO): 1.3(t, 3H), 2.3-2.45(m, 4H), 2.6-2.8(m, 2H), 2.85(q, 2H), 3.4-3.55(m, 4H), 4.45-4.6(m, 2H), 5.4(s, 2H), 6.8-6.9(m, 6H), 7.1-7.7(complex m, 18H), 7.8(dd, 1H), 8.15(d, 1H).

Aufarbeitung

  1. customVolatile material was removed by evaporation
  2. customthe residue purified by flash chromatography
  3. washeluting with methanol/ethyl acetate (1:9 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-cb693278191145d7b8e6d0d39e81d57d
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05219863

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