Benzeneethanamine, alpha-methyl-, phosphate (1:1) → 4-(5-(Benzyloxy)-2-fluoropyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621776

Reaktionsgleichung

Reaktionsgleichung von HRID 1621776
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1.[CH2:28]([O:35][C:36]1[CH:37]=[C:38](B(O)O)[C:39]([F:42])=[N:40][CH:41]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(N)CC1C=CC=CC=1.OP(O)(O)=O.C([O-])(=O)C.[K+]>O.CCO>[CH2:28]([O:35][C:36]1[CH:37]=[C:38]([C:2]2[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[N:3]=2)[C:39]([F:42])=[N:40][CH:41]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

7

Edukt 4

HCID 62885Benzeneethanamine, alpha-methyl-, phosphate (1:1)HCID 517044Potassium AcetateHCID 595482094-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineHCID 665999925-(Benzyloxy)-2-fluoropyridin-3-ylboronic acid

Produkt 1

HCID 665999874-(5-(Benzyloxy)-2-fluoropyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.150 g, 0.390 mmol), 5-(benzyloxy)-2-fluoropyridin-3-ylboronic acid (0.107 g, 0.432 mmol), Amphos (Aldrich) (0.014 g, 0.020 mmol), potassium acetate (Strem) (0.119 g, 1.22 mmol), EtOH (3 mL), and water (0.3 mL) was sealed under N2 and heated in a microwave at 100° C. for 20 min. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (40 g, 10% to 20% EtOAc in hexanes) to give the product as a white solid (0.090 g). m/z (ESI, +ve ion) 552.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 8.17 (d, J=7.31 Hz, 1H); 8.01 (br. s., 1H); 7.31-7.48 (m, 5H); 7.23 (d, J=7.89 Hz, 4H); 6.87 (t, J=7.60 Hz, 4H); 5.13 (s, 2H); 4.81 (d, J=6.28 Hz, 3H); 3.81 (d, J=8.33 Hz, 6H); 2.55 (s, 3H).

Aufarbeitung

  1. customwas sealed under N2
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (40 g, 10% to 20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a8cec71d571d4ae78b3cd655a621962f
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

Verknüpfte Notizen

Wird geladen…