반응 #162062

ord-147cd01489ba4e18a1d4b41c0d4de8fc

반응 방정식

Fc1cnc(-c2c[nH]c3ncc(Cl)cc23)nc1NC1CCCNC1
2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine
Fc1cnc(-c2c[nH]c3ncc(Cl)cc23)nc1N[C@H]1CCCNC1
5b
Fc1cnc(-c2c[nH]c3ncc(Cl)cc23)nc1N[C@H]1CCCNC1
(S)-2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine
CCCN=C=O
propylisocyanate
CCCNC(=O)N1CCCCC1Nc1nc(-c2c[nH]c3ncc(Cl)cc23)ncc1F
desired product
CCCNC(=O)N1CCCCC1Nc1nc(-c2c[nH]c3ncc(Cl)cc23)ncc1F
(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-N-propylpiperidine-1-carboxamide

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The resulting residue was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile)

실험 절차

To a solution of 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine, 5b, (0.020 g, 0.058 mmol) in 1:1 mixture of CH2Cl2/pyridine (2 mL) was added propylisocyanate (0.005 mL, 0.058 mmol). The reaction mixture was stirred at room temperature for 12 hours. The resulting residue was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile) to afford the desired product, 196.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08829007B2uspto-grants-2014_09