Pentanoic Acid → HCID 19349846, compound
Reaction equation
C(O)(=O)CCCC.NC1C=CNC(=O)C=1N(C1C=CC(C2C=CC=CC=2C2NN=NN=2)=CC=1)C.[NH2:35][C:36]1[C:37](=[O:50])[NH:38][CH:39]=[CH:40][C:41]=1[NH:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.Br[CH2:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[C:65]#[N:66])=[CH:55][CH:54]=1>>[CH2:43]([NH:42][C:41]1[CH:40]=[CH:39][NH:38][C:37](=[O:50])[C:36]=1[NH:35][CH2:52][C:53]1[CH:54]=[CH:55][C:56]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[C:65]#[N:66])=[CH:57][CH:58]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1Participants
Procedure
A mixture of 1.02 g of valeric acid, 3.59 g of 4-amino-2-oxo-3-[2'-(tetrazol-5-yl)biphenyl-4-yl-methylamino]-1,2-dihydropyridine (obtainable by reacting 3-amino-4-benzylamino-1,2-dihydro-2-oxopyridine with 4-bromomethyl-2'-cyanobiphenyl to give 4-benzylamino-3-(2'-cyanobiphenyl-4-ylmethylamino)-1,2-dihydro-2-oxopyridine, reacting the latter with trimethyltin azide according to Example 13 to give 4-benzylamino-3-[2'-(tetrazol-5-yl)biphenyl-4-ylmethylamino-1,2-dihydro-2-oxopyridine, and removing the benzyl group by hydrogenolysis] and 50 g of polyphosphoric acid is heated at 140° for 5 hours. 4-amino-2-oxo-3-[N-2'-(tetrazol-5-yl)biphenyl-4-ylmethyl-N-valerylamino]-1,2-dihydro-pyridine and 2-oxo-3-[2'-(tetrazol-5-yl)biphenyl-4-ylmethylamino]-4-valerylamino-1,2-dihydropyridine are formed in situ as intermediates. The mixture is cooled, poured on to ice, rendered alkaline with sodium hydroxide solution and worked up in conventional manner to give 2-butyl-4-oxo-3-[2'-(tetrazol-5-yl)biphenyl-4-ylmethyl]-4,5-dihydro-3H-imidazo[4,5-c]pyridine, m.p. 167°.
Sources & evidence
- ORD record
- ord-f27563dc7af645c094ee2d88a69942de
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06037349
Reaction notes
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