Acetic Acid → HCID 76901355, Verbindung

HRID 880318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 880318
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([NH:7][CH2:8][CH:9]([OH:21])[CH2:10][N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:6].[CH3:25][C:26]1([CH3:33])[CH2:31][C:30](=O)[CH2:29][CH2:28][O:27]1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[CH2:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19][CH2:20][N:11]1[CH2:10][CH:9]([OH:21])[CH2:8][NH:7][C:5](=[O:6])[C:4]1[CH:22]=[CH:23][CH:24]=[C:2]([NH:1][CH:30]2[CH2:29][CH2:28][O:27][C:26]([CH3:33])([CH3:25])[CH2:31]2)[CH:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 17381592,2-Dimethyltetrahydropyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 902415853-amino-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)benzamide

Produkt 1

HCID 76901355HCID 76901355, VerbindungAusbeute 3,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

A solution of 3-amino-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)benzamide (130 mg, 0.4 mmol), 2,2-dimethyldihydro-2H-pyran-4(3H)-one (52 mg, 0.4 mmol) and AcOH (0.1 mL) in MeOH (10 mL). The mixture was stirred at 22° C. for 12 h, then NaBH3CN (76 mg, 1.2 mmol) was added and the resulting mixture was stirred at 22° C. for 2 h. The reaction mixture was concentrated and quenched with water. The aqueous mixture was extracted with DCM, the combined organic layers were concentrated and the residue was purified by prep-HPLC to give the title compound (5.5 mg, Yield 3.1%). 1H NMR (CD3OD, 400 MHz): δ 8.42 (brs, 1H) 7.00-7.33 (m, 7H) 6.84 (d, J=7.8 Hz, 1H) 4.21-4.41 (m, 3H) 3.40-3.92 (m, 8H) 3.11-3.20 (m, 3H) 1.91-2.07 (m, 2H) 1.18-1.44 (m, 8H). LCMS (m/z): 438.3 (M+1).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 22° C. for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customquenched with water
  4. extractionThe aqueous mixture was extracted with DCM
  5. concentrationthe combined organic layers were concentrated
  6. customthe residue was purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b858b50c06664db4be82efbe7d3a42eb
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993555B2

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