Diisopropylethylamine → US9433622, Dmx-131

HRID 55867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 55867
Cl[C:2]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:18]=[N:19][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:21][CH:22]=3)[N:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH:31]1[CH2:35][CH2:34][CH2:33][CH:32]1[CH2:36][C:37]([NH2:39])=[O:38].CCN(C(C)C)C(C)C.CO.C(Cl)(Cl)Cl>CCO>[C:4]([C:3]1[C:2]([N:31]2[CH2:35][CH2:34][CH2:33][CH:32]2[CH2:36][C:37]([NH2:39])=[O:38])=[N:9][CH:8]=[C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:18]=[N:19][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:21][CH:22]=3)[N:11]=2)[CH:6]=1)#[N:5]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 21584188Chloroform methanolHCID 695393622-(Pyrrolidin-2-yl)acetamide hydrochlorideHCID 903695292-Chloro-5-[2-(6-morpholin-4-ylmethyl-pyridin-3-ylamino)-pyrimidin-4-yl]-nicotinonitrile

Produkt 1

HCID 90369534US9433622, Dmx-131

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of compound 18 (100 mg, 0.24 mmol) in EtOH (5 mL) was added 2-(pyrrolidin-2-yl)acetamide-HCl (160 mg, 1.22 mmol) and DIPEA (0.22 mL, 1.22 mmol) at rt and the reaction mixture was heated at reflux for 16 h. The reaction mixture was cooled to rt, concentrated to half of its volume and triturated with n-pentane, the precipitated solid was collected by filtration to obtain DMX-130 (80 mg, 65%) as a white solid. Rf: 0.4 (10% MeOH/CHCl3); (m/z): 499.8 [M+1]+; 1H NMR (300 MHz, DMSO-d6): δ 9.77 (1H, s), 9.13 (1H, d, J=2.4 Hz), 8.87 (1H, d, J=2.4 Hz), 8.66 (1H, d, J=1.8 Hz), 8.50 (1H, d, J=5.1 Hz), 8.16 (1H, dd, J=2.7, 9.0 Hz), 7.46 (1H, d, J=5.7 Hz), 7.38 (1H, d, J=9.0 Hz), 7.30 (1H, br), 6.84 (1H, br), 4.74 (1H, br), 3.97 (1H, br), 3.80-3.76 (1H, br), 3.59-3.53 (6H, m), 2.76-2.70 (1H, m), 2.40 (4H, br), 2.23-2.15 (1H, m), 2.10-2.98 (3H, m), 1.86-1.84 (1H, m).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated to half of its volume
  4. customtriturated with n-pentane
  5. filtrationthe precipitated solid was collected by filtration
  6. customto obtain DMX-130 (80 mg, 65%) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-3168bd04921344eab3ba7adbb865797e
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09433622B2

Notizen zur Reaktion

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