Triethylamine → acetic acid (3-(2-(4-bromophenyl)-1-(4-chlorophenyl)-6-oxo-1H-purin-9(6H)-yl)phenylthio)methyl acetate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:10](=[O:25])[C:11]3C=N[N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([S:23][CH3:24])[CH:18]=4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.ClC1C=CC(N2[C:45](=[O:46])[C:44]3C=NN(C4C=C(C=CC=4)C#N)C=3N=C2C2C=CC(B3[O:68][C:67]([CH3:70])(C)C(C)(C)O3)=CC=2)=CC=1.C([N:75]([CH2:78]C)CC)C.[OH-:80].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)[C:10](=[O:25])[C:11]3[N:75]=[CH:78][N:14]([C:17]4[CH:18]=[C:19]([S:23][CH2:24][O:80][C:67](=[O:68])[CH3:70])[CH:20]=[CH:21][CH:22]=4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[C:45]([OH:46])(=[O:80])[CH3:44]Participants
6
Reactant 4
HCID 8471Triethylamine
HCID 14798Sodium Hydroxide
HCID 247816196-(4-Bromo-phenyl)-5-(4-chloro-phenyl)-1-(3-methylsulfanyl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one
HCID 578994373-{5-(4-Chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl}-benzonitrileProduct 1
Reagents, catalysts & solvents 1
Procedure
4-Bromo-N-(4-chloro-phenyl)-benzamide (3) used is prepared by the following procedure. To a solution of 4-chloroaniline (1, 66.0 g, 517.4 mmol) and 4-bromobenzoyl chloride (2, 109.0 g, 497.5 mmol) in dichloromethane (1200 mL) is added triethyl amine (83.2 mL, 597.0 mmol). The reaction mixture is then poured into 0.05 N sodium hydroxide solution and the resulted suspension is stirred at rt for 1 h. The solid formed is filtered and washed well with water. It is dried in vacuo and used for the next step.
Workup
- customThe solid formed
- filtrationis filtered
- washwashed well with water
- customIt is dried in vacuo
Sources & evidence
- ORD record
- ord-104536930e7145f0b8bd41ddcbd817b4
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722691B2
Reaction notes
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