1-Hydroxybenzotriazole → 2-amino-N-(1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 634484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634484
Cl.[NH2:2][CH:3]([C:5]1[O:6][C:7](=[O:21])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:4].[NH2:22][C:23]1[C:31]([C:32](O)=[O:33])=[C:26]2[N:27]=[CH:28][CH:29]=[CH:30][N:25]2[N:24]=1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:22][C:23]1[C:31]([C:32]([NH:2][CH:3]([C:5]2[O:6][C:7](=[O:21])[C:8]3[C:13]([C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH3:4])=[O:33])=[C:26]2[N:27]=[CH:28][CH:29]=[CH:30][N:25]2[N:24]=1

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 717429442-Aminopyrazolo[1,5-A]pyrimidine-3-carboxylic acidHCID 1181314633-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride2×

Produkt 1

HCID 1181312002-amino-N-(1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamideAusbeute 28,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride (intermediate E2, 50 mg, 0.166 mmol), 2-aminopyrazolo[1,5-a]pyrimidine-3-carboxylic acid (32.5 mg, 0.182 mmol), HOBt (30.4 mg, 0.199 mmol), HBTU (17.25 mg, 0.033 mmol) and DIPEA (61.0 μl, 0.349 mmol) were reacted in DCM (1 ml) at RT for 18 hrs. The crude was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound (20 mg, 28%).

Aufarbeitung

  1. customThe crude was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%)

Quellen und Nachweise

ORD-Eintrag
ord-9f27113e43bb4a8d98415ea5bcac342c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321776B2

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