تفاعل #84176

ord-f888b70187c44de0bd12c1affa653ba4

معادلة التفاعل

CC(C)(C)[SiH2]OC(C)(C)c1ccc(Nc2nccc(-c3ccc(N4CC[C@H](F)C4)c(C#N)n3)n2)cn1
Compound 80
CC(C)(C)[SiH2]OC(C)(C)c1ccc(Nc2nccc(-c3ccc(N4CC[C@H](F)C4)c(C#N)n3)n2)cn1
6-{2-[6-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-3-ylamino]-pyrimidin-4-yl}-3-((S)-3-fluoro-pyrrolidin-1-yl)-pyridine-2-carbonitrile
→
N#Cc1nc(-c2ccnc(Nc3ccc(CO)nc3)n2)ccc1N1CC[C@H](F)C1
title compound
المردود 79.0%
N#Cc1nc(-c2ccnc(Nc3ccc(CO)nc3)n2)ccc1N1CC[C@H](F)C1
3-((S)-3-Fluoro-pyrrolidin-1-yl)-6-[2-(6-hydroxymethyl-pyridin-3-ylamino)-pyrimidin-4-yl]-pyridine-2-carbonitrile
المردود 79.0%

المتفاعلات

CC(C)(C)[SiH2]OC(C)(C)c1ccc(Nc2nccc(-c3ccc(N4CC[C@H](F)C4)c(C#N)n3)n2)cn1
Compound 80
CC(C)(C)[SiH2]OC(C)(C)c1ccc(Nc2nccc(-c3ccc(N4CC[C@H](F)C4)c(C#N)n3)n2)cn1
6-{2-[6-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-3-ylamino]-pyrimidin-4-yl}-3-((S)-3-fluoro-pyrrolidin-1-yl)-pyridine-2-carbonitrile

الكواشف

لا شيء

المذيبات

CC#N.Cl
HCl MeCN

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe solvent was removed in vacuo
  2. 2
    أخرىthe residue triturated with 9:1 EtOAc-MeOH

الإجراء التجريبي

Compound 80 (252 mg, 0.5 mmol) was dissolved in 1:1 2 M HCl-MeCN and the reaction mixture stirred at rt for 5 hours. The solvent was removed in vacuo and the residue triturated with 9:1 EtOAc-MeOH to afford the title compound (152 mg, 79%) as a dark yellow solid; LCMS, Rt=2.40 min (MeOH-FA method), m/z 392 (MH+).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09433622B2uspto-grants-2016_09