Hexane → HCID 44132694, compound
Reaction equation
[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[N:15][C:16]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:17][N:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:26]([C:30]1[CH:34]=[C:33]([N:35]=[C:36]=[O:37])[N:32]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:31]=1)([CH3:29])([CH3:28])[CH3:27].CCCCCC>C1COCC1.C(Cl)Cl>[C:26]([C:30]1[CH:34]=[C:33]([NH:35][C:36]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([O:9][C:10]3[C:19]4=[N:18][CH:17]=[C:16]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[N:15]=[C:14]4[N:13]=[CH:12][CH:11]=3)=[CH:8][C:2]=2[F:1])=[O:37])[N:32]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:31]=1)([CH3:29])([CH3:27])[CH3:28]Participants
6
Procedure
A solution of 2-fluoro-4-(3-morpholinopyrido[2,3-b]pyrazin-8-yloxy)aniline (47 mg, 138 mmol) in dry THF (5 mL) was treated with a solution of 3-tert-butyl-5-isocyanato-1-phenyl-1H-pyrazole (1.1 mL of a 0.25 M solution in CH2Cl2, 275 μmol) at 0° C. A yellow precipitate started to form gradually and after 1 h at RT, hexane (20 mL) was added and the yellow precipitate was filtered off. It was redissolved in MeOH/CH2Cl2 (1:1), evaporated onto silica gel and the product was eluted with a gradient of 0% to 20% MeOH in EtOAc to give the product as a light yellow solid.
Workup
- customto form gradually and after 1 h at RT
- filtrationthe yellow precipitate was filtered off
- dissolutionIt was redissolved in MeOH/CH2Cl2 (1:1)
- customevaporated onto silica gel
- washthe product was eluted with a gradient of 0% to 20% MeOH in EtOAc
Sources & evidence
- ORD record
- ord-9f0ba6567037431ba879fb7ed6234790
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912191B2
Reaction notes
Loading…