1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3,4-dichlorophenyl)-7-{(2E)-4-[isopropyl(methyl)amino]but-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 1887427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887427
Br[CH2:2][CH:3]=[CH:4][C:5]([OH:7])=O.[CH:8]([NH:11][CH3:12])([CH3:10])[CH3:9].[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:34]3[C:33]4[CH2:32][CH2:31][NH:30][CH2:29][C:28]=4[S:27][C:26]=3[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[Cl:20].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:34]3[C:33]4[CH2:32][CH2:31][N:30]([C:5](=[O:7])/[CH:4]=[CH:3]/[CH2:2][N:11]([CH:8]([CH3:10])[CH3:9])[CH3:12])[CH2:29][C:28]=4[S:27][C:26]=3[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[Cl:20]

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78485N-MethylisopropylamineHCID 81531DiisopropylethylamineHCID 841404-Bromo-2-butenoic acidHCID 58116912(3,4-Dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine

Produkt 1

HCID 24748566N-(3,4-dichlorophenyl)-7-{(2E)-4-[isopropyl(methyl)amino]but-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amineAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 4-Bromo-but-2-enoic acid (638 mg, 3.87 mmol) in CH2Cl2 was added isopropylmethyamine (1.1 ml, 10.3 mmol), the mixture was stirred for 2 hours followed by addition of (3,4-dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine (1.0 g, 2.57 mmol), EDCI (493 mg, 2.58 mmol), DIPEA (1.8 ml, 10.3 mmol). The resulting mixture was stirred at RT overnight. Solvents were removed and residue was purified by HPLC to gave the desired compound (500 mg, 13%). 1H-NMR (DMSO-d6) δ 8.46 (m, 1H), 8.39 (s, 1H), 7.88 (m, 1H), 7.62 (m, 1H), 7.42 (t, 1H), 6.67 (m, 1H), 3.94 (m, 2H), 3.87 (m, 4H), 2.75 (m, 2H), 2.11 (s, 3H), 0.96 (d, 6H); LCMS RT=2.72 min, [M+1]+=490.3.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at RT overnight
  2. customSolvents were removed
  3. customresidue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4b7faaaed7e54eaea9d67fe82f15a2f6
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501755B2

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