Acetic Acid → 2,5-Dimethyl-N-{1-[4-(2H-tetrazol-5-yl)phenyl]cyclopropyl}-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxamide

HRID 870063Notes

Reaction equation

HRID 870063 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH:12][C:13]([C:15]3[C:19]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=4)=[C:18]([CH3:31])[S:17][C:16]=3[CH3:32])=[O:14])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[N:33]([Sn](CCCC)(CCCC)CCCC)=[N+:34]=[N-:35].CC(O)=O>C1(C)C=CC=CC=1>[CH3:32][C:16]1[S:17][C:18]([CH3:31])=[C:19]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=2)[C:15]=1[C:13]([NH:12][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([C:1]3[N:33]=[N:34][NH:35][N:2]=3)=[CH:8][CH:7]=2)[CH2:11][CH2:10]1)=[O:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4984872Tributyltin azideHCID 45140392N-[1-(4-cyanophenyl)cyclopropyl]-2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxamide

Product 1

HCID 249529282,5-Dimethyl-N-{1-[4-(2H-tetrazol-5-yl)phenyl]cyclopropyl}-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of N-[1-(4-cyanophenyl)cyclopropyl]-2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxamide from Example 14, Step 2 (174 mg, 0.383 mmol) in toluene (2.5 mL), was added azidotributyltin (317 μL, 1.15 mmol) and the mixture was heated at the reflux temperature. After 20 h, the solution then obtained was allowed to cool to r.t. and AcOH (365 μL) was added. The heterogeneous mixture was stirred for 4 h and the precipitated solid was collected by filtration, successively rinsed with toluene and hexane then dried to afford the desired product as an off-white solid. MS (−APCI): m/z 496 (M−1)−.

Workup

  1. temperaturethe mixture was heated at the reflux temperature
  2. customthe solution then obtained
  3. filtrationthe precipitated solid was collected by filtration
  4. washsuccessively rinsed with toluene and hexane
  5. customthen dried

Sources & evidence

ORD record
ord-745843d0bec24ac6a1746b940aae3cf0
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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