Diisopropylethylamine → HCID 76901360, Verbindung

HRID 880327Notizen

Reaktionsgleichung

[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:50][CH2:51][CH:52]([OH:64])[CH2:53][N:54]1[CH2:63][CH2:62][C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH2:55]1>CN(C=O)C.O>[CH2:55]1[C:56]2[C:61](=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH2:62][CH2:63][N:54]1[CH2:53][CH:52]([OH:64])[CH2:51][NH:50][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([O:7][CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:16][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 22 °C

Versuchsvorschrift

To a solution of 4-((tetrahydro-2H-pyran-4-yl)oxy)benzoic acid (150 mg, 0.67 mmol) in DMF (4 mL) was added DIEA (260 mg, 2.01 mmol), HATU (384 mg, 1.01 mmol) and 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (170 mg, 0.81 mmol). The reaction mixture was stirred at 22° C. for 16 h. The mixture was treated with water and extracted with EA. The organic layer was washed with brine, dried over Na2SO4, concentrated and the residue was was purified by prep-HPLC to give the title compound (206.1 mg, Yield 74.9%). 1H NMR (CD3OD, 400 MHz): δ 7.84 (d, J=8.8 Hz, 2H), 7.26-7.37 (m, 3H), 7.19-7.25 (m, 1H), 7.05 (d, J=8.8 Hz, 2H), 4.59-4.74 (m, 2H), 4.31-4.49 (m, 2H), 3.93-4.01 (m, 2H), 3.86 (brs, 1H), 3.63 (ddd, J=11.7, 8.8, 3.0 Hz, 2H), 3.53 (qd, J=14.0, 5.7 Hz, 3H), 3.37-3.44 (m, 1H), 3.11-3.32 (m, 3H), 2.02-2.12 (m, 2H), 1.69-1.81 (m, 2H). LCMS (m/z): 411.2 (M+1).

Aufarbeitung

extractionextracted with EA
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customthe residue was was purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag: ord-2ebaef3ae7704d0588e5d8ba980e849f
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08993555B2

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