Guanidinoacetic Acid → {[6-Cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}acetic acid
Reaction equation
CN(/[CH:4]=[C:5]1\[CH2:6][C:7]([C:14]2[C:22]3[C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[O:19][C:18]=3[C:17]([O:27][CH3:28])=[CH:16][CH:15]=2)([C:12]#[N:13])[CH2:8][CH2:9][C:10]\1=O)C.[CH2:29]([N:33]=[C:34]([NH2:36])[NH2:35])[C:30]([OH:32])=[O:31].[OH-].[Na+]>CO>[C:12]([C:7]1([C:14]2[C:22]3[C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[O:19][C:18]=3[C:17]([O:27][CH3:28])=[CH:16][CH:15]=2)[CH2:8][CH2:9][C:10]2[N:36]=[C:34]([NH:33][CH2:29][C:30]([OH:32])=[O:31])[N:35]=[CH:4][C:5]=2[CH2:6]1)#[N:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A mixture of the compound obtained in example 6 (100 mg, 0.267 mmol), guanidine acetic acid and sodium hydroxide (54 mg, 1 mol) in 10 ml of methanol was stirred at 60-70° C. for 8 hrs. Methanol was evaporated under vacuum and the reaction mass was diluted with 10 ml of water. The aqueous layer was washed with ether, acidified with 0.1 N HCl to pH 2 and extracted with ethyl acetate. The organic layer was washed with water followed by brine, and concentrated under vacuum. The crude product was crystallized form hexane to give 60 mg (52.45% yields) of a yellow colored solid.
Workup
- customMethanol was evaporated under vacuum
- additionthe reaction mass was diluted with 10 ml of water
- washThe aqueous layer was washed with ether
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- concentrationconcentrated under vacuum
- customThe crude product was crystallized form hexane
- customto give
- custom60 mg (52.45% yields) of a yellow colored solid
Sources & evidence
- ORD record
- ord-8e19d433f362462281b2bdac4d7c2524
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263648B2
Reaction notes
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