Hydrochloric Acid → (E)-N-(2-Isobutoxy-3-methoxybenzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochloride

HRID 2097092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2097092
[CH2:1]([O:5][C:6]1[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:7]=1[CH2:8][N:9]([CH3:26])[C:10](=[O:25])/[CH:11]=[CH:12]/[C:13]1[CH:24]=[N:23][C:16]2[NH:17][C:18](=[O:22])[CH2:19][NH:20][CH2:21][C:15]=2[CH:14]=1)[CH:2]([CH3:4])[CH3:3].[ClH:33]>C(Cl)Cl.C(OCC)C>[ClH:33].[CH2:1]([O:5][C:6]1[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:7]=1[CH2:8][N:9]([CH3:26])[C:10](=[O:25])/[CH:11]=[CH:12]/[C:13]1[CH:24]=[N:23][C:16]2[NH:17][C:18](=[O:22])[CH2:19][NH:20][CH2:21][C:15]=2[CH:14]=1)[CH:2]([CH3:4])[CH3:3]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 16660146HCID 16660146, Verbindung

Produkt 1

HCID 16660145(E)-N-(2-Isobutoxy-3-methoxybenzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochlorideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirring solution of (E)-N-(2-isobutoxy-3-methoxybenzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide (0.108 g, 0.246 mmol) in CH2Cl2 (3 mL) under N2 was treated with HCl (0.12 mL of a 2.0 M solution in diethyl ether, 24 mmol). After stirring for 18 h, the resulting solid was collected by filtration and washed with Et2O (100 mL) and dried. The solid was dissolved in CH2Cl2 (2 mL) and layered with hexanes (5 mL). The resulting solids were collected by filtration, washed with Et2O (50 mL) and dried to yield the target compound (0.052 g, 45%) as a tan solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 11.09-11.07 (m, 1H), 10.03 (br s, 2H), 8.77-8.71 (m, 1H), 8.31-8.24 (m, 1H), 7.62-7.54 (m, 1H), 7.38-7.31 (m, 1H), 7.05-6.59 (m, 2H), 6.68-6.59 (m, 1H), 4.81-4.65 (m, 2H), 4.27-4.23 (m, 2H), 3.85-3.82 (m, 2H), 3.79 (s, 3H), 3.72-3.68 (m, 2H), 3.12-2.88 (m, 3H), 2.06-1.97 (m, 1H), 1.00-0.98 (m, 6H); MS (ESI) m/e 439 (M+H)+.

Aufarbeitung

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with Et2O (100 mL)
  3. customdried
  4. dissolutionThe solid was dissolved in CH2Cl2 (2 mL)
  5. filtrationThe resulting solids were collected by filtration
  6. washwashed with Et2O (50 mL)
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ea2ddb3f2d33429c85891aa9318d00e9
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450307B2

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