Diisopropylethylamine → HCID 49833689, Verbindung

HRID 473914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473914
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:21][CH2:20][CH2:19][N:18]([C:22](Cl)=[O:23])[CH2:17][C:16]=3[CH:25]=2)=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.Cl.[C:36]([CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)#[N:37]>ClCCl>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:21][CH2:20][CH2:19][N:18]([C:22]([N:41]4[CH2:42][CH2:43][CH:38]([C:36]#[N:37])[CH2:39][CH2:40]4)=[O:23])[CH2:17][C:16]=3[CH:25]=2)=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 227446374-Piperidinecarbonitrile hydrochlorideHCID 86672035HCID 86672035, Verbindung

Produkt 1

HCID 49833689HCID 49833689, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dichloromethane (2 mL) was added to 7-[6-(1H-imidazol-2-yl)pyridin-3-yl]-2,3-dihydro-1,4-benzoxazepin-4(5H)-carbonyl chloride was obtained in step 4 followed by diisopropylethylamine (0.12 mL, 0.65 mmol) and 4-cyanopiperidine hydrochloride (25 mg, 0.16 mmol). The mixture was stirred at room temperature for 30 min and then concentrated. Purification of the residue by preparative reverse phase HPLC (0.1% aqueous ammonium acetate-acetonitrile) provided the title compound (18 mg, 32% yield) as a colorless solid. 1H NMR (400 MHz, DMSO-d6): 12.84 (br. S, 1H), 8.86 (d, 1H), 8.11 (m, 2H), 7.71 (d, 1H), 7.61 (dd, 1H), 7.25 (br. s, 1H), 7.10 (br. s, 1H), 7.06 (d, 1H), 4.49 (s, 2H), 4.23 (m, 2H), 3.61 (m, 2H), 3.30 (m, 2H), 3.00 (m, 3H), 1.87 (m, 2H), 1.73 (m, 2H); MS (EI) for C24H24N6O2: 429 (MH+).

Aufarbeitung

  1. customwas obtained in step 4
  2. concentrationconcentrated
  3. customPurification of the residue by preparative reverse phase HPLC (0.1% aqueous ammonium acetate-acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-c498a82bc8dc4839bc7067d1e56c8968
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637499B2

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