Hydrochloric Acid → N-methoxy-N-methyl-3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzamide
Reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25](O)=[O:26])[CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][NH:32][O:33][CH3:34].Cl.CCN=C=NCCCN(C)C.Cl.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:34][O:33][N:32]([CH3:31])[C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([NH:21][C:17]2[CH:16]=[C:15]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:9][CH:10]=3)[N:20]=[CH:19][N:18]=2)[CH:23]=1Participants
8
Reactant 6
HCID 313Hydrochloric Acid
HCID 757711-Hydroxybenzotriazole
HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)
HCID 81531Diisopropylethylamine
HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 577083343-(6-(4-Phenoxyphenylamino)pyrimidin-4-ylamino)benzoic acidProduct 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzoic acid (0.05 g, 0.12 mmol) in DMF (2 mL) were added MeNH—OMe.HCl (0.0084 g, 0.12 mmol), EDCl.HCl (0.0361 g, 0.18 mmol), HOBT (0.0084 g, 0.062 mmol) and DIPEA (0.023 g, 0.18 mmol). The reaction mixture was stirred at room temperature for 1 h and was quenched with water. A white solid was isolated by filtration and dried under vacuum to give N-methoxy-N-methyl-3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzamide (0.025 g, 44.5%) as a white solid.
Workup
- customwas quenched with water
- customA white solid was isolated by filtration
- customdried under vacuum
Sources & evidence
- ORD record
- ord-9870b8d9449d49d7bc8a8f7d45798cc5
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748606B2
Reaction notes
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