Reaktion #505529

ord-3f11bb6f9a7a4acdad2d85f0c085e225

Reaktionsgleichung

O
H2O
COc1ccc(C(=O)NCc2cccc(C(=O)Nc3nc4c(s3)C[C@H](NC(=O)C(F)(F)F)CC4)c2)cc1Cl
3-chloro-4-methoxy-N-{3-[(R)-6-(2,2,2-trifluoro-acetylamino)-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl]-benzyl}-benzamide
O=C([O-])[O-].[K+].[K+]
K2CO3
→
COc1ccc(C(=O)NCc2cccc(C(=O)Nc3nc4c(s3)C[C@H](N)CC4)c2)cc1Cl
N-[3-((R)-6-Amino-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl)-benzyl]-3-chloro-4-methoxy-benzamide
Ausbeute 77.2%

Edukte

—
desired material
O
H2O
COc1ccc(C(=O)NCc2cccc(C(=O)Nc3nc4c(s3)C[C@H](NC(=O)C(F)(F)F)CC4)c2)cc1Cl
3-chloro-4-methoxy-N-{3-[(R)-6-(2,2,2-trifluoro-acetylamino)-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl]-benzyl}-benzamide
O=C([O-])[O-].[K+].[K+]
K2CO3

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF
CO
MeOH

Reaktionsbedingungen

Temperatur
55°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigepurified via prep HPLC (5%-70% CH3CN/H2O)

Vorschrift

Dissolved 3-chloro-4-methoxy-N-{3-[(R)-6-(2,2,2-trifluoro-acetylamino)-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl]-benzyl}-benzamide (520 mg, 0.92 mmol) in 5 mL of MeOH and added 5 mL of H2O. To this was added K2CO3 (500 mg, 3.62 mmol) and the mixture was heated overnight at 55° C. LC-MS analysis indicated the desired material. Dissolved in 5 mL of DMF and purified via prep HPLC (5%-70% CH3CN/H2O) to give 334.6 mg of N-[3-((R)-6-Amino-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl)-benzyl]-3-chloro-4-methoxy-benzamide. MS, electrospray 471.2 (M+H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08093266B2uspto-grants-2012_01