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

HRID 75880

반응식

HRID 75880 반응식
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3N=C(N[C@H](C4C=CC(F)=CC=4)C)C(CNC(=O)C)=[CH:12][C:11]=3F)[CH:5]=2)[CH2:3][CH2:2]1.[CH3:32][CH2:33][N:34](C(C)C)C(C)C.[F:41][C:42]1[CH:47]=[CH:46][C:45]([C@@H:48]([NH2:50])[CH3:49])=[CH:44][CH:43]=1>>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:11]=[CH:12][N:34]=[C:33]([NH:50][C@H:48]([C:45]4[CH:46]=[CH:47][C:42]([F:41])=[CH:43][CH:44]=4)[CH3:49])[CH:32]=3)[CH:5]=2)[CH2:2][CH2:3]1

참가 물질

4

반응물 3

HCID 81531DiisopropylethylamineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 67460058(S)-N-((6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)pyridin-3-yl)methyl)acetamide

생성물 1

HCID 86620605N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-[(S)-1-(4-fluoro-phenyl)-ethyl]-pyridine-2,4-diamine

반응 조건

온도
160 °C

실험 절차

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.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified 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)

출처 및 근거

ORD 기록
ord-4a3a8f6b5d5a40b286da03c8be90d033
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835465B2

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