1,2-Dichloroethane → (E)-N-methyl-3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)-N-((3-methylbenzo[b]thiophen-2-yl)methyl)acrylamide

HRID 1880013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1880013
C(Cl)CCl.Cl.[CH3:6][N:7]1[C:14](=[O:15])[CH2:13][CH2:12][NH:11][C:10]2[N:16]=[CH:17][C:18](/[CH:20]=[CH:21]/[C:22]([OH:24])=O)=[CH:19][C:9]=2[CH2:8]1.C1C=CC2N(O)N=NC=2C=1.[CH3:35][NH:36][CH2:37][C:38]1[S:42][C:41]2[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=2[C:39]=1[CH3:47].C(N(C(C)C)C(C)C)C>CN(C=O)C.C(#N)CC.C(OCC)(=O)C>[CH3:35][N:36]([CH2:37][C:38]1[S:42][C:41]2[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=2[C:39]=1[CH3:47])[C:22](=[O:24])/[CH:21]=[CH:20]/[C:18]1[CH:17]=[N:16][C:10]2[NH:11][CH2:12][CH2:13][C:14](=[O:15])[N:7]([CH3:6])[CH2:8][C:9]=2[CH:19]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22593745N-methyl(3-methylbenzo[b]thiophen-2-yl)methanamineHCID 68413470(E)-3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)acrylic acid hydrochloride

Produkt 1

HCID 24891613(E)-N-methyl-3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)-N-((3-methylbenzo[b]thiophen-2-yl)methyl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 86641869DMF propionitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

EDC (54 mg, 0.28 mmol) was added to a suspension of (E)-3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)acrylic acid hydrochloride (70 mg, 0.23 mmol), HOBt (34 mg, 0.25 mmol), N-methyl(3-methylbenzo[b]thiophen-2-yl)methanamine (48 mg, 0.25 mmol) and (i-Pr)2EtN (0.20 mL, 1.2 mmol) in 5 mL of DMF:propionitrile (4:1). The mixture was allowed to stir for 17 h at 40° C. The mixture was cooled to room temperature and diluted with ethyl acetate (40 mL) and washed with water (50 mL) and NaHCO3 (50 mL), dried over MgSO4 and dried under high vacuum. The solid was then subjected to purification on Prep HPLC to obtain the product as a fluffy white solid. Yield 54 mg (54%); 1H NMR (400 MHz, CDCl3) δ 10.41 (bs, 1H), 8.08 (s, 1H), 7.79-7.68 (m, 3H), 7.59 (d, J=15.2 Hz, 1H), 7.40 (m, 2H), 6.95-6.86 (m, 1H), 4.96 (s, 2H), 4.72 (bs, 2H), 3.90 (s, 2H), 3.15 (m, 5H), 2.84 (s, 3H), 2.46 (s, 3H); ESI MS m/z 435 [C24H26N4O2S+H]+

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water (50 mL) and NaHCO3 (50 mL)
  3. dry with materialdried over MgSO4
  4. customdried under high vacuum
  5. customThe solid was then subjected to purification on Prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-47bd8d1bf1cf4bd3a83c9f43cd65f67d
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318720B2

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