Triethylamine → HCID 57082339, compound

HRID 583408Notes

Reaction equation

HRID 583408 reaction equation
C(N(CC)CC)C.FC(F)(F)C(O)=O.[CH2:15]([O:17][C:18](=[O:35])[CH2:19][CH2:20][CH2:21][CH:22]([NH:33][CH3:34])[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)[CH3:16].[F:36][C:37]([F:52])([F:51])[C:38]1[CH:39]=[C:40]([CH:44]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:46]=1)[C:41](Cl)=[O:42]>O1CCCC1>[CH2:15]([O:17][C:18](=[O:35])[CH2:19][CH2:20][CH2:21][CH:22]([N:33]([C:41](=[O:42])[C:40]1[CH:44]=[C:45]([C:47]([F:48])([F:49])[F:50])[CH:46]=[C:38]([C:37]([F:36])([F:51])[F:52])[CH:39]=1)[CH3:34])[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 67565478HCID 67565478, compound

Product 1

HCID 57082339HCID 57082339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.16 ml (8.32 mmol) of triethylamine and then a solution of 947 mg (2.38 mmol) of 6-(1H-indol-3-yl)-5-methylamino-hexanoic acid ethyl ester trifluoracetic acid salt in 10 ml of tetrahydrofuran are added dropwise at 0° C. in the course of 30 minutes to a solution of 0.49 ml (2.61 mmol) of 97% 3,5-bistrifluoromethyl-benzoyl chloride in 10 ml of tetrahydrofuran. The mixture is stirred at room temperature for 18 hours, then filtered and washed with 10 ml of tetrahydrofuran. The filtrate is concentrated by evaporation and diethyl ether is added. The mixture is then filtered over silica gel and the filtrate is concentrated by evaporation. The title compound is obtained in the form of a brown oil. MS (EI): 528 (M+.), 483, 398, 257, 241, 130. TLC: ethyl acetate, Rf =0.66.

Workup

  1. filtrationfiltered
  2. washwashed with 10 ml of tetrahydrofuran
  3. concentrationThe filtrate is concentrated by evaporation and diethyl ether
  4. additionis added
  5. filtrationThe mixture is then filtered over silica gel
  6. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-36a3c59f400d4bd8a431a4c44f111200
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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