Isopropanol → 2-(2-Amino-6-phenoxy-4h-pyrido[3,4-d]pyrimidin-3-yl)-3,n-dimethyl-n-phenethyl-butyramide hydrochloride salt
Reaction equation
[NH2:1][C:2]1[C:3]([CH2:15][NH:16][CH:17]([CH:30]([CH3:32])[CH3:31])[C:18]([N:20]([CH3:29])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:19])=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(O)(C)C.[N:37]#[C:38]Br.[Cl:40]CCl>>[ClH:40].[NH2:37][C:38]1[N:16]([CH:17]([CH:30]([CH3:32])[CH3:31])[C:18]([N:20]([CH3:29])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:19])[CH2:15][C:3]2[CH:4]=[C:5]([O:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:6]=[CH:7][C:2]=2[N:1]=1Participants
5
Reactant 4
Product 1
Procedure
A solution of 2-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-3,N-dimethyl-N-phenethyl-butyramide (1.69 g, 3.9 mmol) and isopropyl alcohol (10 mL) was added cyanogen bromide in dichloromethane (1.3 mL, [3M]) and the resulting mixture was stirred at room temperature for 16 hours. The solvent was evaporated to yield a brown solid. The brown solid was purified by reverse phase chromatography. The solvent was evaporated from the desired fractions, and the solute was treated with 1N HCl to yield the title compound as a solid, as its corresponding hydrochloride salt.
Workup
- customThe solvent was evaporated
- customto yield a brown solid
- customThe brown solid was purified by reverse phase chromatography
- customThe solvent was evaporated from the desired fractions
- additionthe solute was treated with 1N HCl
Sources & evidence
- ORD record
- ord-fe43abca38544525a56879bb21a7a7be
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531545B2
Reaction notes
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