Reacción #717714

ord-1a0f47997951415f948244dcb9df5e77

Ecuación de reacción

CSc1cn(-c2ncc(-c3ccccn3)cn2)c2cc(C(=O)N3C[C@@H]4C[C@H]3CN4C(=O)OC(C)(C)C)ccc12
244c
CSc1cn(-c2ncc(-c3ccccn3)cn2)c2cc(C(=O)N3C[C@@H]4C[C@H]3CN4C(=O)OC(C)(C)C)ccc12
(1S,4S)-tert-Butyl 5-(3-(methylthio)-1-(5-(pyridin-2-yl)pyrimidin-2-yl)-1H-indole-6-carbonyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
CSc1cn(-c2ncc(Br)cn2)c2cc(C(=O)O)ccc12
1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid
CNCC(=O)OC.Cl
methyl 2-(methylamino)acetate hydrochloride
→
COC(=O)CN(C)C(=O)c1ccc2c(SC)cn(-c3ncc(Br)cn3)c2c1
Methyl 2-(1-(5-bromopyrimidin-2-yl)-N-methyl-3-(methylthio)-1H-indole-6-carboxamido)acetate

Reactantes

CSc1cn(-c2ncc(-c3ccccn3)cn2)c2cc(C(=O)N3C[C@@H]4C[C@H]3CN4C(=O)OC(C)(C)C)ccc12
244c
CSc1cn(-c2ncc(-c3ccccn3)cn2)c2cc(C(=O)N3C[C@@H]4C[C@H]3CN4C(=O)OC(C)(C)C)ccc12
(1S,4S)-tert-Butyl 5-(3-(methylthio)-1-(5-(pyridin-2-yl)pyrimidin-2-yl)-1H-indole-6-carbonyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
—
Amide
CSc1cn(-c2ncc(Br)cn2)c2cc(C(=O)O)ccc12
1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid
CNCC(=O)OC.Cl
methyl 2-(methylamino)acetate hydrochloride

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

Amide coupling of 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid (2.0 g, 5.49 mmol) with methyl 2-(methylamino)acetate hydrochloride (1.53 g, 10.9 mmol) analogously to the protocol 244c). White solid. Yield: 0.6 g (24% of theory)

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09315490B2uspto-grants-2016_04