Diisopropylethylamine → HCID 18617839, Verbindung

HRID 1264239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264239
[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[C:29]#[N:30].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(O)(C(F)(F)F)=O.O.C(O)(C(F)(F)F)=O.C(#N)C>CN(C=O)C>[C:29]([C:23]1[C:22]2[C:26](=[CH:27][CH:28]=[C:20]([CH2:19][CH2:18][NH:17][C:12](=[O:14])[C:11]3[CH:10]=[CH:9][C:8]([CH:5]4[CH2:4][CH2:3][C:2](=[O:1])[NH:7][CH2:6]4)=[CH:16][CH:15]=3)[CH:21]=2)[NH:25][CH:24]=1)#[N:30]

Komponenten

8

Edukt 6

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11217658HCID 11217658, VerbindungHCID 18617602HCID 18617602, VerbindungHCID 21924481TFA acetonitrileHCID 22392675Trifluoroacetic acid water

Produkt 1

HCID 18617839HCID 18617839, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(6-Oxo-piperidin-3-yl)-benzoic acid (190 mg, 0.87 mmol, reference example 65) and 5-(2-amino-ethyl)-1H-indole-3-carbonitrile (161 mg, 0.87 mmol, reference example 2) is dissolved in anhydrous DMF (3 mL). To this solution is added diisoproplyethylamine (330 μl, 1.9 mmol), followed by HBTU (330 mg, 0.87 mmol) and allowed to stir at room temperature overnight (16 hours). The product is isolated by Reverse-Phase chromatography of the crude reaction mixture (Dynamax C-18 60 A (5×30 cm), 50 ml/min, λ@ 220 nm, 10-70% B in 15 minutes, A: 0.1% TFA/water, B: 0.1% TFA/acetonitrile). 1H NMR (300 MHz, DMSO) δ 1.94 (m, 2H), 2.26 (m, 2H), 2.92 (t, J=7.1, 2H), 3.19 (m, 1H), 3.48 (m, 2H), 3.46 (m, 2H), 7.13 (d, J=8.4, 1H), 7.15 (d, J=1.4, 2H), 7.36 (d, J=8.3, 2H), 7.43 (d, J=8.5, 1H), 7.46 (s, 1H), 7.55 (d, J=2.5, 1H), 7.73 (d, J=8.3, 2H), 8.17 (d, J=3.0, 1H), 8.47 (t, J=5.5, 1H). MS (Ion spray) m/z 387 (M+H)+.

Aufarbeitung

  1. customThe product is isolated by Reverse-Phase chromatography of the crude
  2. customreaction mixture (Dynamax C-18 60 A (5×30 cm), 50 ml/min, λ@ 220 nm, 10-70% B in 15 minutes

Quellen und Nachweise

ORD-Eintrag
ord-4fcf2a382dfd4ceeba68e80d9cb7c222
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541505B1

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