2-(4-Cyanophenoxy)acetic acid → 3-(4-Cyanophenyloxyacetylamino)-4-methylaminophenyl-(1-methoxycarbonylmethyl-cyclohex-1-yl)-ketone
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].[NH2:14][C:15]1[CH:16]=[C:17]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]2([C:34]([C:36]2([CH2:51][C:52]([O:54][CH3:55])=[O:53])[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]2[C:42]2[CH:47]=[CH:46][C:45]([NH:48][CH3:49])=[C:44]([NH2:50])[CH:43]=2)=[O:35])[CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:18]=[CH:19][C:20]=1[NH:21][CH3:22]>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][CH2:10][C:11]([NH:50][C:44]2[CH:43]=[C:42]([CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][C:36]3([C:34]([C:24]3([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]3[C:17]3[CH:18]=[CH:19][C:20]([NH:21][CH3:22])=[C:15]([NH:14][C:11](=[O:13])[CH2:10][O:9][C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=4)[CH:16]=3)=[O:35])[CH2:51][C:52]([O:54][CH3:55])=[O:53])[CH:47]=[CH:46][C:45]=2[NH:48][CH3:49])=[O:13])=[CH:7][CH:8]=1)#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
620 mg (3.5 mmol) of 4-cyanophenyloxyacetic acid and 570 mg (3.5 mmol) of 1,1′-carbonylduimidazole were refluxed in 50 mL of tetrahydrofuran for 15 minutes. Then 1.0 g (3.28 mmol) of 3-amino-4-methylaminophenyl-(1-methoxycarbonylmethylcyclohex-1-yl) ketone were added and the mixture was boiled for a further 4 hours. Then the solvent was evaporated off and the crude product thus obtained was purified by column chromatography (150 g silica gel; eluant: dichloromethane with 0 to 2% ethanol). Yield: 1.4 g (93% of theory), C26H29N3O5 (463.5); Rf value: 0.44 (silica gel; dichloromethane/ethanol=19:1).
Workup
- customThen the solvent was evaporated off
Sources & evidence
- ORD record
- ord-eab50584c89e451b8dac6aca375e3ca1
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06710055B2
Reaction notes
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