1,1'-Carbonyldiimidazole → 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].C([N:21]1[CH:25]=[CH:24]N=C1)(N1C=CN=C1)=O.[NH2:26][C:27]1[CH:28]=[C:29]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][C:36]2([C:46]([C:48]2([CH2:63][C:64]([O:66][CH3:67])=[O:65])[CH2:53][CH2:52][CH2:51][CH2:50][CH:49]2[C:54]2[CH:59]=[CH:58][C:57]([NH:60][CH3:61])=[C:56]([NH2:62])[CH:55]=2)=[O:47])[CH2:41][C:42]([O:44][CH3:45])=[O:43])[CH:30]=[CH:31][C:32]=1[NH:33][CH3:34]>O1CCCC1>[C:25]([C:24]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11]([NH:62][C:56]2[CH:55]=[C:54]([CH:49]3[CH2:50][CH2:51][CH2:52][CH2:53][C:48]3([C:46]([C:36]3([CH2:41][C:42]([O:44][CH3:45])=[O:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH:35]3[C:29]3[CH:30]=[CH:31][C:32]([NH:33][CH3:34])=[C:27]([NH:26][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:28]=3)=[O:47])[CH2:63][C:64]([O:66][CH3:67])=[O:65])[CH:59]=[CH:58][C:57]=2[NH:60][CH3:61])=[O:13])=[CH:5][CH:4]=1)#[N:21]Participants
5
Reactant 3
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'-carbonyl-diimidazole were refluxed in 50 ml of tetrahydrofuran for 15 minutes. Then 1.0 g (3.28 mMol) of 3-amino-4-methylaminophenyl-(1-methoxycarbonylmethyl-cyclohex-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-ddabcb585bcd457daccfe398c6e30fe7
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06087380
Reaction notes
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