Diisopropylethylamine → HCID 66711064, Verbindung

HRID 1262074

Reaktionsgleichung

Reaktionsgleichung von HRID 1262074
[O:1]1[C:5]2[C:6]([C:10]3[N:18]4[C:13]([CH:14]=NC(O)=[N:17]4)=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[CH:20]([N:23](CC)C(C)C)(C)C.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[NH2:44][C:45]1[C:59]([O:60][CH3:61])=[CH:58][C:48]2[CH2:49][CH2:50][N:51]([CH2:54][C@H:55]([OH:57])[CH3:56])[CH2:52][CH2:53][C:47]=2[CH:46]=1>CN(C=O)C>[O:1]1[C:5]2[C:6]([C:10]3[N:18]4[C:13]([CH:14]=[CH:20][N:23]([NH:44][C:45]5[C:59]([O:60][CH3:61])=[CH:58][C:48]6[CH2:49][CH2:50][N:51]([CH2:54][C@H:55]([OH:57])[CH3:56])[CH2:52][CH2:53][C:47]=6[CH:46]=5)[NH:17]4)=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 4176748N-Propyl-Methyl Piperidinium Bis(trifluoroMethylsulfonyl)ImideHCID 66711392(R)-1-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-propan-2-olHCID 178517424HCID 178517424, Verbindung

Produkt 1

HCID 66711064HCID 66711064, VerbindungAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of 7-(2,3-Dihydro-benzofuran-7-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (0.100 g, 0.395 mmol, 1.05 eqv) and N,N-Diisopropylethylamine (0.28 mL, 4.22 eqv) in anhydrous DMF (1 mL) in a 10 mL sealed tube was added N-Phenylbis(trifluoromethane-sulfonimide (0.148 g, 1.105 eqv.). The mixture was stirred at room temperature for 1 h and to it (R)-1-(7-amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-propan-2-ol (0.094 mg, 0.38 mmol, 1.00 eqv.) was added. The reaction mixture was heated at 70° C. for 2 h, concentrated in vacuo and purified via prepTLC (silica gel; eluant: 6% methanol in methylene chloride) to afford (R)-1-{7-[7-(2,3-Dihydro-benzofuran-7-yl)-pyrrolo[2,1-f]triazin-2-ylamino]-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-propan-2-ol as a dark brown solid (0.018 g, 10%). MP>200° C. (decomp.). LCMS (E/I+) 486.16 (M+H). 1H NMR (CDCl3) δ 8.80 (s, 1H), 8.30 (d, 2H, J=6.50 Hz), 7.45 (s, 1H), 7.30 (s, 2H), 7.00 (dd, 1H, J=6.00H, 6.00 Hz), 6.80 (d, 1H, J=6.00 Hz), 6.65 (s, 1H), 4.80 (t, 2H, J=6.00 Hz), 3.90 (broad, 1H), 3.80 (s, 3H), 3.30 (t, 2H, J=6.00 Hz), 2.90-2.10 (overlapping m, 11H), 1.10 (d, 3H, J=6.00 Hz).

Aufarbeitung

  1. customsealed tube
  2. additionwas added
  3. concentrationconcentrated in vacuo
  4. custompurified via prepTLC (silica gel; eluant: 6% methanol in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-6b6c01bd5e134d769b0c831276b587ed
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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