Diisopropylethylamine → HCID 66970630, compound
Reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:44][C:45]1[CH:65]=[CH:64][C:48]([O:49][C:50]2[C:55]([C:56]3[CH:61]=[CH:60][N:59]=[C:58]([NH:62][CH3:63])[N:57]=3)=[CH:54][CH:53]=[CH:52][N:51]=2)=[CH:47][CH:46]=1>C(Cl)(Cl)Cl>[F:1][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([NH:44][C:45]1[CH:46]=[CH:47][C:48]([O:49][C:50]2[C:55]([C:56]3[CH:61]=[CH:60][N:59]=[C:58]([NH:62][CH3:63])[N:57]=3)=[CH:54][CH:53]=[CH:52][N:51]=2)=[CH:64][CH:65]=1)=[O:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 2-fluoro-3-pyridinecarboxylic acid (1.06 g, 7.50 mmol) and HATU (3.11 g, 8.18 mmol) in CHCl3 at ambient temperature under nitrogen was added n,n-diisopropylethylamine (2.38 ml, 13.6 mmol) via syringe. The mixture was allowed to stir for 5 min, at which point 4-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine (2.00 g, 6.82 mmol) was added. The reaction was allowed to stir 16 h, resulting in the formation of a fine precipitate. The reaction was filtered, rinsing with 2× dichloromethane and the solid dried in vacuo to give 2-fluoro-N-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)nicotinamide as a tan solid. MS m/z=417 [M+1]+. Calc'd for C22H17FN6O2: 416.41.
Workup
- additionwas added
- customresulting in the formation of a fine precipitate
- filtrationThe reaction was filtered
- washrinsing with 2× dichloromethane
- customthe solid dried in vacuo
Sources & evidence
- ORD record
- ord-12c2e8723b7d46d5a7849c10e83174fc
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476434B2
Reaction notes
Loading…