Pentanoic Acid → HCID 178484505, compound

HRID 1734183Notes

Reaction equation

C(O)(=O)CCCC.[NH2:8][C:9]1[CH:14]=[CH:13][N:12]([CH:15]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:27])[C:10]=1[NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]2[NH:46][N:45]=[N:44][N:43]=2)=[CH:32][CH:31]=1.NC1C(=O)N(C(C(=O)N(C)C)C2C=CC=CC=2)C=CC=1N[CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.BrCC1C=CC(C2C=CC=CC=2C#N)=CC=1.C(NC1C=CN(C(C(=O)N(C)C)C2C=CC=CC=2)C(=O)C=1NCC1C=CC(C2C=CC=CC=2C#N)=CC=1)C1C=CC=CC=1.C[Sn](N=[N+]=[N-])(C)C>>[CH2:55]([NH:8][C:9]1[CH:14]=[CH:13][N:12]([CH:15]([C:22](=[O:26])[N:23]([CH3:24])[CH3:25])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:27])[C:10]=1[NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]2[NH:46][N:45]=[N:44][N:43]=2)=[CH:32][CH:31]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

Reactant 6

HCID 7991Pentanoic Acid

HCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

HCID 5104973Azido(trimethyl)stannane

HCID 22363550HCID 22363550, compound

HCID 57203391HCID 57203391, compound

HCID 178484506HCID 178484506, compound

Product 1

HCID 178484505HCID 178484505, compound

Procedure

A mixture of 1.02 g of valeric acid, 5.2 g of 4-amino-1,2-dihydro-2-oxo-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethylamino]-1-(α-N,N-dimethylcarbamoylbenzyl)pyridine [obtainable by reaction of 3-amino-4-benzylamino-1,2-dihydro-2-oxo-1-(α-N,N-dimethylcarbamoylbenzyl)pyridine with 4-bromomethyl-2'-cyanobiphenyl to give 4-benzylamino-3-(2'-cyanobiphenyl-4-ylmethylamino)-1,2-dihydro-2-oxo-1-(α-N,N-dimethylcarbamoylbenzyl)pyridine, reaction with trimethyltin azide to give 4-benzylamino-1,2-dihydro-2-oxo-3-(2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethylamino)-1-(α-N,N-dimethylcarbamoylbenzyl)pyridine, and hydrogenolytic cleavage of the benzyl group] and 50 g of polyphosphoric acid is heated for 5 hours at 140°. 4-Amino-1,2-dihydro-2-oxo-2-(N-(2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl)-N-valerylamino)-1-(α-N,N-dimethylcarbamoylbenzyl)pyridine and 1,2-dihydro-2-oxo-3-(2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethylamino)-1-(α-N,N-dimethylcarbamoylbenzyl)-4-valerylaminopyridine are formed in situ as intermediates. The mixture is cooled, poured onto ice, rendered alkaline with sodium hydroxide solution and worked up in a conventional manner to give 2-butyl-3-(2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl)-4,5-dihydro-4-oxo-5-(α-N,N-dimethylcarbamoylbenzyl)-3H-IP.

Workup

customto give

Sources & evidence

ORD record: ord-d3ab29f1823448c0aee45c1acceb167d
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05532276

Reaction notes

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