HCID 59612419, Verbindung → [5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amine

HRID 1890000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890000
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([NH:19][C:20]3[N:37]=[C:23]4[CH:24]=[CH:25][CH:26]=[C:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[CH2:34][O:35][CH3:36])[N:22]4[N:21]=3)[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH3:36][O:35][CH2:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:27]1[N:22]2[N:21]=[C:20]([NH:19][C:16]3[CH:17]=[CH:18][C:11]4[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=4[CH:15]=3)[N:37]=[C:23]2[CH:24]=[CH:25][CH:26]=1

Komponenten

4

Edukt 1

HCID 59612419HCID 59612419, Verbindung

Produkt 1

HCID 59612550[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amineAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

7-[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester (105.0 mg, 0.210 mmol) was stirred in 3M trifluoroacetic acid in dichloromethane (10 mL) for 30 minutes. The volatiles were evaporated and the residue was dissolved in ethyl acetate and washed with sodium carbonate solution (2×) and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. Product isolated as a foam (0.079 g, 89%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.64 (d, J=7.7 Hz, 1H), 7.58-7.41 (m, 5H), 7.25-7.21 (m, 1H), 7.16-7.04 (m, 1H), 6.99 (d, J=8.0 Hz, 1H), 6.91-6.87 (m, 1H), 4.35 (br s, 2H), 3.20 (s, 3H), 2.98-2.81 (m, 8H), 2.02 (br s, 1H). MS=400 (MH)+.

Aufarbeitung

  1. customThe volatiles were evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with sodium carbonate solution (2×) and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fd4cb99a9128437096fa020dc1432e55
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501936B2

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