Dimethylformamide → HCID 178441526, compound

HRID 1636899Notes

Reaction equation

HRID 1636899 reaction equation
CN(C=O)C.[CH2:6]([C:10]1[N:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]#[N:46])=[CH:35][CH:34]=2)[C:13]2[C:14](=[O:30])[N:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:16]=[CH:17][C:12]=2[N:11]=1)[CH2:7][CH2:8][CH3:9].[Cl-].C([NH+](CC)CC)C.[N-:55]=[N+:56]=[N-:57].[Na+]>O.C(OCC)(=O)C>[CH2:6]([C:10]1[N:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]3[NH:57][N:56]=[N:55][N:46]=3)=[CH:35][CH:34]=2)[C:13]2[C:14](=[O:30])[N:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:16]=[CH:17][C:12]=2[N:11]=1)[CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 10098914HCID 10098914, compoundHCID 12698378Triethylazanium chloride

Product 1

HCID 178441526HCID 178441526, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1450 ml of DMF, 219.7 g of 2-butyl-3-(2'-cyano-biphenyl-4-ylmethyl)-4,5-dihydro-4-oxo-5-(o-ethoxycarbonyl-benzyl)-3H-imidazo[4,5-c]pyridine, 166.5 g of triethylammonium chloride and 78.6 g of sodium azide is heated to 120° for 22 hours. After cooling, the mixture is worked up conventionally with ethyl acetate and water, the crude product is purified several times by suspending it in ethanol and filtering, and 2-butyl-4,5-dihydro-4-oxo-3-[2'-(tetrazol-5-yl)-biphenyl-4-ylmethyl]-5-(o-ethoxycarbonyl-benzyl)-3H-imidazo[4,5-c]-pyridine is obtained; m.p. 203-20°.

Workup

  1. temperatureis heated to 120° for 22 hours
  2. temperatureAfter cooling
  3. customthe crude product is purified several times
  4. filtrationfiltering

Sources & evidence

ORD record
ord-7475c0933d254a0db585df0456c47c92
Source dataset
uspto-grants-2000_03
Patent number
US06037349

Reaction notes

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