Réaction #8380

ord-ea1e8d4f720a4896a3c22d426cba3c83

Équation de réaction

COC(=O)C=Cc1ccc2nccc(-c3c(-c4cccc(C)n4)nn4c3CCC4)c2c1
3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-6-yl}-acrylic acid methyl ester
[Li+].[OH-]
lithium hydroxide
CO.N
ammonia methanol
Cc1cccc(-c2nn3c(c2-c2ccnc4ccc(C=CC(=O)O)cc24)CCC3)n1
desired product
Rendement 181.6%
Cc1cccc(-c2nn3c(c2-c2ccnc4ccc(C=CC(=O)O)cc24)CCC3)n1
3-{4-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-6-yl}-acrylic acid
Rendement 181.6%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreRemove the solvent
  2. 2
    LavageElute the column with methanol (50 mL)

Mode opératoire

Dissolve 3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-6-yl}-acrylic acid methyl ester (0.040 g, 0.1 mmol) in methanol/water (3:1, 2 mL). Add lithium hydroxide (0.010 g, 0.25 mmol) and stir the mixture 18 h. Remove the solvent then load the residue on a SCX resin column with methanol. Elute the column with methanol (50 mL) then with 2 N ammonia/methanol to give the desired product as a pale yellow solid 0.036 g (92%)

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07087626B2uspto-grants-2006_08