Hydrochloric Acid → methyl 5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrole-3-carboxylate
Reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:43][C:44]1[CH:45]=[C:46]([CH:63]=[CH:64][CH:65]=1)[O:47][C:48]1[CH:53]=[CH:52][N:51]=[C:50]([C:54]2[NH:58][CH:57]=[C:56]([C:59]([O:61][CH3:62])=[O:60])[CH:55]=2)[CH:49]=1.Cl>CN(C=O)C.O>[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([NH:43][C:44]1[CH:45]=[C:46]([CH:63]=[CH:64][CH:65]=1)[O:47][C:48]1[CH:53]=[CH:52][N:51]=[C:50]([C:54]2[NH:58][CH:57]=[C:56]([C:59]([O:61][CH3:62])=[O:60])[CH:55]=2)[CH:49]=1)=[O:9]Participants
8
Reactant 5
HCID 313Hydrochloric Acid
HCID 781273-Methyl-2-furoic acid
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 58167884methyl 5-[4-(3-aminophenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxylateProduct 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 3-methyl-2-furoic acid (490 mg, 3.88 mmol), HATU (1.71 g, 4.5 mmol) and N,N-diisopropylethylamine (1.0 g, 7.8 mmol) in anhydrous DMF (10 ml) was stirred at room temperature for 10 minutes, followed by addition of methyl 5-[4-(3-aminophenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxylate (1.0 g, 3.24 mmol). The mixture was stirred at 50° C. for 2 hours and poured into 100 ml of water. 2M HCl was added dropwise until pH=4˜5. The precipitates were filtered, washed with water and dried in vacuo to give methyl 5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrole-3-carboxylate as white solid.
Workup
- stirringThe mixture was stirred at 50° C. for 2 hours
- filtrationThe precipitates were filtered
- washwashed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-482f9248c4ab4953861d020abd052769
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328103B2
Reaction notes
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