تفاعل #332693

ord-9da1059bb7894579b79ba6d0a4fec94f

معادلة التفاعل

C[C@@H]1CN(c2c(CO)nc3c(-c4ccccn4)noc3c2Cl)C[C@H](C)O1
(7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-(pyridin-2-yl)isoxazolo[4,5-b]pyridin-5-yl)methanol
C[C@@H]1CN(c2c(CO)nc3c(-c4ccccn4)noc3c2Cl)C[C@H](C)O1
Intermediate 201
C[C@@H]1CN(c2c(CO)nc3c(-c4ccccn4)noc3c2Cl)C[C@H](C)O1
(7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-(pyridin-2-yl)isoxazolo[4,5-b]pyridin-5-yl)methanol
C[C@@H]1CN(c2c(C=O)nc3c(-c4ccccn4)noc3c2Cl)C[C@H](C)O1
title compound
المردود 42.0%
C[C@@H]1CN(c2c(C=O)nc3c(-c4ccccn4)noc3c2Cl)C[C@H](C)O1
7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-(pyridin-2-yl)isoxazolo[4,5-b]pyridine-5-carbaldehyde
المردود 42.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe reaction was filtered over Celite®
  2. 2
    تركيزthe filtrate concentrated under vacuum
  3. 3
    أخرىto give clear oil
  4. 4
    أخرىThe oil was purified on short bed of silica using 20-30% acetone in n-hexane

الإجراء التجريبي

To a stirring solution of (7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-(pyridin-2-yl)isoxazolo[4,5-b]pyridin-5-yl)methanol (Intermediate 201, 0.39 g, 1.04 mmol) in dichloromethane (20 mL) was added Manganese dioxode (0.543 g, 6.24 mmol). The mixture was allowed to stir 2 days at room temperature. The reaction was filtered over Celite®, and the filtrate concentrated under vacuum to give clear oil. The oil was purified on short bed of silica using 20-30% acetone in n-hexane to give 0.16 g (42%) of the title compound as a yellow solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08658641B2uspto-grants-2014_02