Diisopropylethylamine → N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-[(S)-1-(4-fluoro-phenyl)-ethyl]-pyridine-2,4-diamine
Reaction equation
[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]1Participants
4
Reactant 3
Product 1
Conditions
- Temperature
- 160 °C
Procedure
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.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- 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)
Sources & evidence
- ORD record
- ord-23641923c4e34006b3f88a83c17edfab
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324252B2
Reaction notes
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