Cyclohexanecarboxylic acid → 7,7-Dimethyl-2-cyclohexyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[CH:15]1([C:21](O)=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH3:13][C:5]1([CH3:14])[C:4]2[C:8](=[CH:9][C:10]3[NH:11][C:21]([CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)=[N:1][C:2]=3[CH:3]=2)[NH:7][C:6]1=[O:12]Participants
3
Procedure
Analogously to Example 1, from 960 mg. (5.0 mmole) 5,6-diamino-3,3-dimethylindolin-2-one and 640 mg. (5.0 mmole) cyclohexanecarboxylic acid, after 1.5 hours at 240° C., there is obtained 1.37 g. of crude product. 300 mg. thereof are purified over a silica gel column (elution agent: dichloromethane/methanol 9:1 v/v). After removal of the solvent in a vacuum, there is obtained a greenish oil which is crystallised with diethyl ether. There are obtained 192 mg. (53% of theory) of the title compound in the form of pale brown crystals; m.p. 315°-318° C.
Workup
- customthere is obtained 1.37 g
- customthereof are purified over a silica gel column (elution agent: dichloromethane/methanol 9:1 v/v)
- customAfter removal of the solvent in a vacuum
- customthere is obtained a greenish oil which
- customis crystallised with diethyl ether
- customThere are obtained 192 mg
Sources & evidence
- ORD record
- ord-ac834cfbe0d54ff18ded75bf5a30b54a
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04730003
Reaction notes
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