HCID 21717622, compound → HCID 178439175, compound

HRID 1386485Notes

Reaction equation

HRID 1386485 reaction equation
CC1C(C(C2C=CC(C#N)=CC=2)C=C)=CC2C(C)(C)CCC(C)(C)C=2C=1.[CH3:27][C:28]1([CH3:52])[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[C:34]2[CH:33]=[C:32]([CH:40]([C:43]3[CH:51]=[CH:50][C:46]([C:47](O)=[O:48])=[CH:45][CH:44]=3)[CH:41]=[CH2:42])[CH:31]=[CH:30][C:29]1=2.O.[NH2:54][C:55]1[NH:59][N:58]=[N:57][N:56]=1>C1COCC1>[CH3:27][C:28]1([CH3:52])[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[C:34]2[CH:33]=[C:32]([CH:40]([C:43]3[CH:51]=[CH:50][C:46]([C:47]([NH:54][C:55]4[NH:59][N:58]=[N:57][N:56]=4)=[O:48])=[CH:45][CH:44]=3)[CH:41]=[CH2:42])[CH:31]=[CH:30][C:29]1=2

Participants

5

Reactant 3

HCID 21717622HCID 21717622, compoundHCID 21717629HCID 21717629, compound2×HCID 178509300HCID 178509300, compound

Product 1

HCID 178439175HCID 178439175, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 equivalent of N,N′-carbonyldi-imidazole (Aldrich, 0.46 g, 0.29 mmol) is added, at ambient temperature to a solution of acid (E) 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]benzoic acid (0.10 g, 0.29 mmol) in 5 ml of anhydrous THF. Half an hour later, 1 equivalent of 5-aminotetrazole monohydrate (Aldrich, 0.30 g, 0.29 mmol) is added. The magnetic stirring is continued for 15 hours 30 minutes. A white precipitate forms in the reaction medium. The mixture is evaporated to dryness and 10 ml of HCl is added. The solution is filtered and the filtrate washed with water and with methanol. After drying one night in a desiccator (with P2O5), 15 mg of a white solid is obtained the compound (E) 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]-N-(tetrazol-5-yl)-benzamide (compound CB73364) (yield=12%).

Workup

  1. customThe mixture is evaporated to dryness and 10 ml of HCl
  2. additionis added
  3. filtrationThe solution is filtered
  4. washthe filtrate washed with water and with methanol
  5. dry with materialAfter drying one night in a desiccator (with P2O5)

Sources & evidence

ORD record
ord-e0f00d010d03442697b2a5016188d27f
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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