Diisopropylethylamine → N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]-2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]acetamide

HRID 1506627

Reaktionsgleichung

Reaktionsgleichung von HRID 1506627
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]([F:41])([F:40])[C:27]1[C:35]2[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=2[N:29]([CH2:36][C:37]([OH:39])=O)[N:28]=1.CCN(C(C)C)C(C)C.[C:51]1([CH2:57][CH:58]([C:60]2[N:64]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)[N:63]=[N:62][CH:61]=2)[NH2:59])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C=O)C>[C:51]1([CH2:57][CH:58]([NH:59][C:37](=[O:39])[CH2:36][N:29]2[C:30]3[CH2:31][CH2:32][CH2:33][CH2:34][C:35]=3[C:27]([C:26]([F:25])([F:41])[F:40])=[N:28]2)[C:60]2[N:64]([C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)[N:63]=[N:62][CH:61]=2)[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 788039[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]acetic acidHCID 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 90281444N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]-2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

HATU (40 mg, 0.105 mmol) was added to a solution of 2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetic acid (25.0 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 compound. 1H NMR (400 MHz, DMSO) δ 9.02 (d, J=7.9 Hz, 1H), 7.96 (s, 1H), 7.58-7.42 (m, 3H), 7.30-7.18 (m, 2H), 7.18-7.06 (m, 3H), 7.00-6.86 (m, 2H), 5.06 (q, J=7.6 Hz, 1H), 4.74-4.61 (m, 2H), 2.98 (td, J=13.6, 6.4 Hz, 2H), 2.43 (s, 2H), 2.37-2.17 (m, 2H), 1.61 (d, J=5.9 Hz, 4H). MS (m/z) 495 [M+H]+.

Quellen und Nachweise

ORD-Eintrag
ord-0a65a477532546b7848ecf889a7a8168
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09220710B2

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