Triethylamine → HCID 68851040, compound

HRID 492287

Reaction equation

HRID 492287 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:3]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])C=CC=CC=1.C([N:32]([CH2:35]C)CC)C.[CH2:37]([NH:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]2[N:62]([C:63]([C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[N:61]=[N:60][N:59]=2)=[CH:48][CH:47]=1)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>C1C=CC=CC=1>[CH2:37]([N:44]([CH2:45][C:46]1[CH:47]=[CH:48][C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]2[N:62]([C:63]([C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)([C:76]3[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=3)[C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[N:61]=[N:60][N:59]=2)=[CH:50][CH:51]=1)[C:35](=[O:20])[NH:32][C:3]1[C:7]([F:12])=[CH:8][C:9]([F:11])=[CH:10][C:2]=1[F:1])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 5203732,4,6-Trifluorobenzoic acidHCID 68851238HCID 68851238, compound

Product 1

HCID 68851040HCID 68851040, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2,4,6-Trifluorobenzoic acid (148.8 mg), diphenylphosphoryl azide (223.3 mg) and triethylamine (105.1 mg) were added to benzene (8 mL) and the mixture was heated under reflux. Fifty minutes later, a solution of N-heptyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (393.7 mg) in benzene (3 mL) was added to the reaction mixture, and under reflux, heating was continued. Upon elapsed time of 45 minutes after the addition of the solution, the reaction mixture was concentrated under reduced pressure. Ethyl acetate (40 mL) was added to the residue, and the resulting mixture was washed successively with 5% hydrochloric acid, water, a saturated sodium bicarbonate solution and brine (40 mL, each). The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (hexane/ethyl acetate) to afford N′-heptyl-N-(2,4,6-trifluorophenyl)-N′-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]urea as a colorless amorphous mass (369.1 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureunder reflux
  4. temperatureheating
  5. additionUpon elapsed time of 45 minutes after the addition of the solution
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionEthyl acetate (40 mL) was added to the residue
  8. washthe resulting mixture was washed successively with 5% hydrochloric acid, water
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b98e816bba8844feb006a99d8dff52de
Source dataset
uspto-grants-2009_05
Patent number
US07531576B2

Linked notes

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