Diisopropylethylamine → HCID 58864391, Verbindung

HRID 2250154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250154
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH:18]([NH2:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:26](=[O:27])C1.C(N(CC)C(C)C)(C)C.[NH:51]1[CH2:56][CH2:55][CH:54]([N:57]2[CH2:66][C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[NH:59][C:58]2=[O:67])[CH2:53][CH2:52]1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH:18]([C:19]([O:21][CH3:22])=[O:20])[NH:23][C:26]([N:51]3[CH2:52][CH2:53][CH:54]([N:57]4[CH2:66][C:65]5[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=5)[NH:59][C:58]4=[O:67])[CH2:55][CH2:56]3)=[O:27])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 676246Di(succinimido) carbonateHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 59639683Methyl α-amino-1-[(1,1-dimethylethoxy)carbonyl]-1H-indazole-5-propanoate

Produkt 1

HCID 58864391HCID 58864391, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5-(2-amino-2-methoxycarbonyl-ethyl)-indazole-1-carboxylic acid tert-butyl ester (307 mg, 0.96 mmol), N,N-disuccinimidyl carbonate (246 mg, 0.961 mmol), and N,N-diisopropylethylamine (0.67 mL, 3.84 mmol) in methylene chloride was stirred for 30 min at room temperature. 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (238 mg, 1.03 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The solvent was evaporated and the residue subjected to flash chromatography using methylene chloride/methanol/triethylamine (93:5:2) as eluent, giving the product (259 mg, 47%). 1H-NMR (CDCl3, 300 MHz) δ 8.13-8.10 (m, 2H), 7.48 (br s, 1H), 7.31 (dd, J=8.8, 1.6 Hz, 1H), 7.16 (t, J=8.0 Hz, 1H), 7.05 (d, J=7.0 Hz, 1H), 6.94 (t, J=7.7 Hz, 1H), 6.82 (s, 1H), 6.66 (d, J=8.0 Hz, 1H), 4.98 (d, J=7.7 Hz, 1H), 4.87-4.81 (m, 1H), 4.58-4.49 (m, 1H), 4.26 (s, 2H), 4.05-3.97 (m, 2H), 3.74-3.67 (m, 4H), 3.29-3.23 (m, 2H), 2.93-2.84 (m, 2H), 1.76-1.62 (m, 1H), 1.70 (s, 9H), 1.48-1.42 (m, 1H). Mass spec.: 577 (MH)+.

Aufarbeitung

  1. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ec57b1fce1fa43ed9ca57ca06ae91cba
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314883B2

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