Sodium Hydroxide → 6-Methoxymethyl-3-(3-(4-(pyridin-2-ylmethoxy)-benzyl)-isoxazol-5-yl)pyridin-2-ylamine

HRID 640452

Reaktionsgleichung

Reaktionsgleichung von HRID 640452
[NH2:1][C:2]1[C:7]([C:8]2[O:12][N:11]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH:9]=2)=[CH:6][CH:5]=[C:4]([CH2:21][O:22][CH3:23])[N:3]=1.[OH-].[Na+].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][Cl:33].Cl.[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:41]Cl>O.CO>[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][Cl:33].[CH3:23][O:22][CH2:21][C:4]1[N:3]=[C:2]([NH2:1])[C:7]([C:8]2[O:12][N:11]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:41][C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=4)=[CH:16][CH:15]=3)[CH:9]=2)=[CH:6][CH:5]=1

Komponenten

8

Edukt 4

HCID 14798Sodium Hydroxide2×HCID 23392Picolyl chloride hydrochlorideHCID 23393Picolyl chlorideHCID 592552174-(5-(2-Amino-6-methoxymethyl-pyridin-3-yl)isoxazol-3-ylmethyl)-phenol

Produkt 2

HCID 23393Picolyl chlorideHCID 592552866-Methoxymethyl-3-(3-(4-(pyridin-2-ylmethoxy)-benzyl)-isoxazol-5-yl)pyridin-2-ylamineAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a methanol (1.5 mL) solution of 4-(5-(2-amino-6-methoxymethyl-pyridin-3-yl)isoxazol-3-ylmethyl)-phenol (50 mg, 0.16 mmol) described in Manufacturing Example 166-1-1 was added a 1 N sodium hydroxide aqueous solution (160 μL, 0.16 mmol), which was concentrated under a reduced pressure. N,N-dimethylformamide (1.5 mL) was added to the residue thus obtained at room temperature, and 2-picolyl chloride (29 mg, 0.23 mmol; this 2-picolyl chloride was prepared by adding a 5 N sodium hydroxide aqueous solution to 2-picolyl chloride hydrochloride) was added to the reaction mixture at the same temperature. The reaction mixture was stirred for 100 minutes at the same temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=4:1) to obtain the title compound (32 mg, 52%).

Aufarbeitung

  1. concentrationwas concentrated under a reduced pressure
  2. additionN,N-dimethylformamide (1.5 mL) was added to the residue
  3. customthus obtained at room temperature
  4. additionwas added to the reaction mixture at the same temperature
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride
  7. concentrationwas concentrated under a reduced pressure
  8. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-7601f2eacbca430cba2a17e711fba694
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691882B2

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