Reaktion #171671

ord-19f83d1386b44a96af1387a89aff5482

Reaktionsgleichung

COC(=O)c1ccc(N(C)C(=O)c2cc3c(s2)-c2ccc(C#N)cc2OCC3)c(Cl)c1
methyl 3-chloro-4-(8-cyano-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)benzoate
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HBTU
CN
methylamine
CCN(C(C)C)C(C)C
DIEA
[Li+].[OH-]
lithium hydroxide
→
CNC(=O)c1ccc(N(C)C(=O)c2cc3c(s2)-c2ccc(C#N)cc2OCC3)c(Cl)c1
180
CNC(=O)c1ccc(N(C)C(=O)c2cc3c(s2)-c2ccc(C#N)cc2OCC3)c(Cl)c1
N-(2-chloro-4-(methylcarbamoyl)phenyl)-8-cyano-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Edukte

COC(=O)c1ccc(N(C)C(=O)c2cc3c(s2)-c2ccc(C#N)cc2OCC3)c(Cl)c1
methyl 3-chloro-4-(8-cyano-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)benzoate
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HBTU
—
carboxylic acid
CN
methylamine
CCN(C(C)C)C(C)C
DIEA
[Li+].[OH-]
lithium hydroxide

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
ClCCl
dichloromethane
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Following Example 91, methyl 3-chloro-4-(8-cyano-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)benzoate was saponified with lithium hydroxide in THF and water, then the carboxylic acid was coupled with methylamine, HBTU, DIEA in dichloromethane to give 180. MS: (ESI+) 452.1

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846762B2uspto-grants-2014_09