Triethylamine → HCID 178477684, Verbindung

HRID 1959411

Reaktionsgleichung

Reaktionsgleichung von HRID 1959411
[NH2:1][C:2]1[C:3]([C:19](O)=O)=[N:4][C:5]([C:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:12][CH:13]=2)=[CH:6][N:7]=1.[CH3:22][C:23]1[CH:24]=[C:25]([NH2:30])[C:26]([NH2:29])=[CH:27][CH:28]=1.C(OP(C#N)(OCC)=O)C.C(N(CC)CC)C>COCCOC>[CH2:17]([S:14]([N:11]1[CH2:12][CH:13]=[C:8]([C:5]2[N:4]=[C:3]([C:19]3[NH:29][C:26]4[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][C:25]=4[N:30]=3)[C:2]([NH2:1])=[N:7][CH:6]=2)[CH2:9][CH2:10]1)(=[O:16])=[O:15])[CH3:18]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 103323,4-DiaminotolueneHCID 76257Diethyl cyanophosphonateHCID 667448673-amino-6-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazine-2-carboxylic acid

Produkt 1

HCID 178477684HCID 178477684, VerbindungAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 3-amino-6-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazine-2-carboxylic acid (100 mg, 0.320 mmol), 4-methylbenzene-1,2-diamine (39.12 mg, 0.320 mmol), diethoxyphosphorylformonitrile (47.83 uL, 0.320 mmol) and triethylamine (44.63 uL, 0.320 mmol) in DME (1 mL) were heated in a microwave at 170° C. for 90 min. After this time the reaction mixture was filtered and purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, and freeze-dried to give the title compound (46.8 mg, 21% Yield). 1H NMR (400.0 MHz, DMSO) d 8.34 (s, 1H), 7.57 (d, J=8.1 Hz, 1H), 7.46 (s, 1H), 7.11 (d, J=8.0 Hz, 1H), 6.78 (s, 1H), 4.00 (d, J=2.8 Hz, 2H), 3.50 (t, J=5.7 Hz, 2H), 3.16 (q, J=7.4 Hz, 2H), 2.78 (s, 2H), 2.46 (s, 3H) and 1.25 (t, J=7.4 Hz, 3H) ppm; MS (ES+) 399

Aufarbeitung

  1. filtrationAfter this time the reaction mixture was filtered
  2. custompurified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  3. customThe fractions were collected
  4. customfreeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-44bcdf01035241e1b5a2e7e95076439b
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410112B2

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