Diisopropylethylamine → N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-[(S)-1-(4-fluoro-phenyl)-ethyl]-pyridine-2,4-diamine

참여 물질

역할	이름	HCID	투입량
반응물	Diisopropylethylamine	HCID 81531	—
반응물	(S)-1-(4-Fluorophenyl)-ethylamine	HCID 2779063	—
반응물	(S)-N-((6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)pyridin-3-yl)methyl)acetamide	HCID 67460058	—
생성물	N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-[(S)-1-(4-fluoro-phenyl)-ethyl]-pyridine-2,4-diamine	HCID 86620605	—

반응 조건

온도	160 °C

반응 단계

A mixture of (2-chloro-pyridin-4-yl)-(5-cyclopropyl-1H-pyrazole-3-yl)-amine (Method 4; 0.116 g, 0.49 mmol), DIEA (0.20 ml, 1.18 mmol), and (S)-1-(4-fluoro-phenyl)-ethylamine (1.0 ml, 7.4 mmol) was heated to 160° C. in a sealed tube for 2 days. The reaction mixture was concentrated under reduced pressure and purified by reverse-phase prep HPLC (column: mC-PACK-ODS-AQ, 250×20 nm, 3.0×50 mm; 5-95% gradient MeCN (0.05% TFA) in water (0.1% TFA); flow rate: 10.0 ml/min). 1H NMR (400 MHz) δ 0.696 (m, 2H), 0.958 (m, 2H), 1.49 (m, 4H), 4.75 (q, 1H), 5.60 (s, 1H), 7.19 (t, 2H), 7.29 (t, 1H), 7.42 (t, 3H), 7.6 (s, 1H), 9.89 (s, 1H). MS: Calcd.: 337. Found: [M+H]+ 338.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08835465B2
출처 데이터셋	uspto-grants-2014_09
ORD ID	ord-4a3a8f6b5d5a40b286da03c8be90d033
출처 메모	uspto-grants-2014_09