Reaktion #1555361

ord-09f7c2fda9b545e0b6a9d19435195fbc

Reaktionsgleichung

CC(C)(C)OC(=O)N[C@H]1CCc2nc(NC(=O)c3cccc(Cn4cc(-c5ccc(C#N)cc5)cn4)c3)sc2C1
((S)-2-{3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester
O=C([O-])[O-].[Na+].[Na+]
Na2CO3
→
N#Cc1ccc(-c2cnn(Cc3cccc(C(=O)Nc4nc5c(s4)C[C@@H](N)CC5)c3)c2)cc1
N—((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzamide
Ausbeute 75.0%

Edukte

CC(C)(C)OC(=O)N[C@H]1CCc2nc(NC(=O)c3cccc(Cn4cc(-c5ccc(C#N)cc5)cn4)c3)sc2C1
((S)-2-{3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester
O=C([O-])[O-].[Na+].[Na+]
Na2CO3

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2
O=C(O)C(F)(F)F
TFA

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenConcentrate
  2. 2
    Sonstigethe reaction
  3. 3
    SonstigeTriturate the residue with CH2Cl2
  4. 4
    Filtrationfilter the product

Vorschrift

Stir ((S)-2-{3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester (0.38 g, 0.69 mmol) in 2 mL CH2Cl2 and 2 mL TFA for 3 h in a capped flask. Concentrate the reaction and bring to alkaline pH with aq. Na2CO3. Triturate the residue with CH2Cl2 and filter the product to give 0.23 g 75% yield of N—((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzamide as a beige solid. MS, ES+ 455.73 (M+H), rt 1.39 min.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09000154B2uspto-grants-2015_04