5-Hydroxyindoleacetic Acid → 2-(5-hydroxy-1H-indol-3-yl)-N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]acetamide

HRID 1506635

Reaktionsgleichung

Reaktionsgleichung von HRID 1506635
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[CH2:35][C:36]([OH:38])=O.CCN(C(C)C)C(C)C.[C:48]1([CH2:54][CH:55]([C:57]2[N:61]([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[N:60]=[N:59][CH:58]=2)[NH2:56])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[OH:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[CH2:35][C:36]([NH:56][CH:55]([C:57]1[N:61]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[N:60]=[N:59][CH:58]=1)[CH2:54][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:38]

Komponenten

6

Edukt 4

HCID 18265-Hydroxyindoleacetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 902812472-phenyl-1-(1-phenyl-1H-1,2,3-triazol-5-yl)ethanamine

Produkt 1

HCID 902812762-(5-hydroxy-1H-indol-3-yl)-N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

HATU (40 mg, 0.105 mmol) was added to a solution of 2-(5-hydroxy-1H-indol-3-yl)acetic acid (19.2 mg, 0.1 mmol) and DIPEA (0.02 mL, 0.12 mmol) in DMF (0.3 mL). After 10 minutes, 9D (26.5 mg, 0.1 mmol) in 0.2 mL of DMF was added to the reaction. The reaction was stirred for 2 hours. LC/MS shows desired product with a small amount of acid. Purified reaction mixture on prep reverse phase HPLC using 20-80% B over 20 min. (A=0.1% TFA/H2O; B=0.1% TFA/Acetonitrile). Combined pure fractions as determined by LC/MS and lyophilized to provide the desired product. 1H NMR (400 MHz, CD3OD) δ 7.76 (s, 1H), 7.47 (t, J=7.5 Hz, 1H), 7.39 (t, J=7.6 Hz, 2H), 7.21-7.01 (m, 6H), 6.96 (s, 1H), 6.84 (d, J=1.9 Hz, 1H), 6.78 (d, J=6.8 Hz, 2H), 6.68 (dd, J=8.6, 2.3 Hz, 1H), 5.46 (s, 2H), 5.21 (t, J=7.6 Hz, 1H), 2.96 (ddd, J=21.5, 13.3, 7.6 Hz, 2H); MS (m/z) 438 [M+H]+.

Quellen und Nachweise

ORD-Eintrag
ord-b9a3c52a6e754d8fb0397816574848a6
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09220710B2

Verknüpfte Notizen

Wird geladen…