Propionic Acid → (+/-)9-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-3-quinoxalin-2-yl-non-4-enoic acid ethyl ester

HRID 860083

Reaction equation

HRID 860083 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][NH:8][C:9]2[N:14]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19](O)[CH:20]=[CH:21][C:22]3[CH:31]=[N:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(O)(=O)CC.Cl.[Cl-].[Na+].O.[C:44]([CH3:54])(OCC)([O:48]CC)[O:45][CH2:46][CH3:47]>>[CH2:46]([O:45][C:44](=[O:48])[CH2:54][CH:21]([C:22]1[CH:31]=[N:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1)[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16][CH2:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:8][CH2:7][C:6]2[CH:33]=[CH:34][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:14]=1)[CH3:47]

Participants

5

Reactant 4

HCID 1032Propionic AcidHCID 66221Triethyl orthoacetate2×HCID 69665953(+/-)7-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-quinoxalin-2-yl-hept-1-en-3-olHCID 131718760Hydrochloric acid brine

Product 1

HCID 69666596(+/-)9-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-3-quinoxalin-2-yl-non-4-enoic acid ethyl esterYield 48%

Conditions

Temperature
150 °C

Procedure

A solution of the allylic alcohol 22-3 (0.26 g, 0.57 mmol) in (EtO)3CMe (10 mL) was treated with 100 μL of a 1 mL solution of (EtO)3CMe containing 10 μL of propionic acid. The yellow solution was heated at 150° C. for 90 minutes. The solution was cooled to room temperature and poured into 1N HCl/brine. The mixture was extracted with CHCl3, dried, concentrated, and purified on silica gel (90:5:5 CHCl3:EtOAc:MeOH) to give 0.143 g (48%) of 22-4.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe mixture was extracted with CHCl3
  3. customdried
  4. concentrationconcentrated
  5. custompurified on silica gel (90:5:5 CHCl3:EtOAc:MeOH)

Sources & evidence

ORD record
ord-9f0c2d2ae3554ba4842efdb93e0c1261
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Linked notes

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