Triethylamine → HCID 57814706, Verbindung

HRID 521613

Reaktionsgleichung

Reaktionsgleichung von HRID 521613
[C:1]([NH:4][C@@H:5]([CH2:9][CH2:10][S:11][CH3:12])[C:6]([OH:8])=O)(=[O:3])[CH3:2].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:45][CH2:46][CH2:47][O:48][C:49]1[CH:54]=[CH:53][C:52]([NH:55][C:56](=[O:65])[C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([O:63][CH3:64])[CH:58]=2)=[CH:51][C:50]=1[C:66]1[N:70]([CH3:71])[N:69]=[CH:68][CH:67]=1>ClCCl>[C:1]([NH:4][C@@H:5]([CH2:9][CH2:10][S:11][CH3:12])[C:6]([NH:45][CH2:46][CH2:47][O:48][C:49]1[CH:54]=[CH:53][C:52]([NH:55][C:56](=[O:65])[C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([O:63][CH3:64])[CH:58]=2)=[CH:51][C:50]=1[C:66]1[N:70]([CH3:71])[N:69]=[CH:68][CH:67]=1)=[O:8])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 448580N-acetyl-L-methionineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67265457HCID 67265457, Verbindung

Produkt 1

HCID 57814706HCID 57814706, VerbindungAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(S)-2-acetamido-4-(methylthio)butanoic acid (17.8 mg, 1.25 eq), triethylamine (20.8 mL, 2.0 eq) and HATU (35.4 mg, 1.25 eq) were dissolved in 3 mL of dichloromethane and stirred at room temperature for 10 minutes. At this time N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide hydrochloride (30 mg, 74.5 μmol) dissolved in 2.0 mL of dichloromethane was added and the reaction was stirred at room temperature for 3 hr. The solvents were evaporated under a stream of nitrogen and it was purified by HPLC. The proper fractions were collected and lyophilized to afford the title compound as a white solid in 57.3% yield. LCMS m/z (%)=540 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ ppm 2.01 (s, 4H), 2.07 (s, 3H), 2.38-2.44 (m, 2H), 3.46-3.65 (m, 2H), 3.85 (s, 3H), 3.88 (s, 3H), 4.03-4.12 (m, 2H), 4.45-4.53 (m, 1H), 6.39 (d, J=2.02 Hz, 1H), 7.02 (d, J=9.60 Hz, 1H), 7.11 (dt, J=4.80, 2.53 Hz, 1H), 7.38-7.42 (m, 2H), 7.43-7.46 (m, 1H), 7.63-7.71 (m, 2H), 7.86 (s, 1H)

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature for 3 hr
  3. customThe solvents were evaporated under a stream of nitrogen and it
  4. customwas purified by HPLC
  5. customThe proper fractions were collected

Quellen und Nachweise

ORD-Eintrag
ord-1136de85f3c940d8ad92093b4336dc44
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328107B2

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