Pentanoic Acid → HCID 178447239, compound

HRID 1654254Notes

Reaction equation

HRID 1654254 reaction equation
C(O)(=O)CCCC.NC1C=CN(CC(=O)N(C)C)C(=O)C=1NCC1C=CC([C:30]2[CH:34]=[CH:33][S:32][C:31]=2[C:35]2[NH:39][N:38]=[N:37][N:36]=2)=CC=1.N[C:41]1[C:42](=[O:61])[N:43](CC(=O)N(C)C)[CH:44]=[CH:45][C:46]=1NCC1C=CC=CC=1.[CH2:62]([NH:69][CH:70]1[CH:75]=[CH:74][N:73]([CH2:76][C:77](=[O:81])[N:78]([CH3:80])[CH3:79])[CH2:72][C:71]1=O)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.C[Sn](N=[N+]=[N-])(C)C>>[NH:36]1[C:35]([C:31]2[S:32][CH:33]=[CH:34][C:30]=2[N:69]([CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:70]2([NH:43][C:42](=[O:61])[CH2:41][CH2:46][CH2:45][CH3:44])[CH:75]=[CH:74][N:73]([CH2:76][C:77](=[O:81])[N:78]([CH3:80])[CH3:79])[CH:72]=[CH:71]2)=[N:39][N:38]=[N:37]1

Participants

6

Reactant 5

HCID 7991Pentanoic AcidHCID 5104973Azido(trimethyl)stannaneHCID 18999937HCID 18999937, compoundHCID 20080009HCID 20080009, compoundHCID 178484603HCID 178484603, compound

Product 1

HCID 178447239HCID 178447239, compound

Procedure

A mixture of 1.02 g of valeric acid, 4.50 g of 4-amino-1,2-dihydro-2-oxo-3-(4-(2-(1H-5-tetrazolyl)-3-thienyl)benzylamino)-1-(N,N-dimethylcarbamoylmethyl)pyridine [obtainable by reaction of 3-amino-4-benzylamino-1,2-dihydro-2-oxo-1-(N,N-dimethylcarbamoylmethyl)pyridin with IIa to give 4-benzylamino-3-oxo-1-(N,N-dimethylcarbamoylmethyl)pyridine, reaction with trimethyltin azide to give 4-benzylamino-1,2-dihydro-2-oxo-3-(4-(2-(1H-5-tetrazolyl)-3-thienyl)benzylamino)-1-(N,N-dimethylcarbamoylmethyl)pyridine and hydrogenolytic removal of the benzyl group] and 50 g of polyphosphoric acid is heated for 5 hours at 140°. 4-Amino-1,2-dihydro-2-oxo-3-(N-4-(2-(1H-5-tetrazolyl)-3-thienyl)benzyl-N-valerylamino)-1-(N,N-dimethylcarbamoylmethyl)pyridine and 1,2-dihydro-2-oxo-3-(4-(2-(1H-5-tetrazolyl)-3-thienylbenzylamino)-1-(N,N-dimethylcarbamoylmethyl)-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 the conventional manner, and gives 2-butyl-3-(4-(2-(1H-5 -tetrazolyl)-3-thienyl)benzyl-4,5-dihydro-4-oxo-5-(N,N-dimethylcarbamoylmethyl)-3H-IP.

Workup

  1. customto give
  2. customto give
  3. custom4-benzylamino-1,2-dihydro-2-oxo-3-(4-(2-(1H-5-tetrazolyl)-3-thienyl)benzylamino)-1-(N,N-dimethylcarbamoylmethyl)pyridine and hydrogenolytic removal of the benzyl group] and 50 g of polyphosphoric acid
  4. temperatureis heated for 5 hours at 140°

Sources & evidence

ORD record
ord-345c1bfdf2fb471598103e9fd353320b
Source dataset
uspto-grants-1995_04
Patent number
US05405964

Reaction notes

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