Triethylamine → HCID 15013790, compound

HRID 1198971Notes

Reaction equation

HRID 1198971 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:35][CH:36]([C:38](=[O:42])[N:39]([CH3:41])[CH3:40])[CH3:37])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26]C(C)(C)C)=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>O1CCOCC1.O>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:35][CH:36]([C:38](=[O:42])[N:39]([CH3:41])[CH3:40])[CH3:37])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 15013789HCID 15013789, compound

Product 1

HCID 15013790HCID 15013790, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(N,N-dimethylcarbamoyl)propyl]indol-1-ylmethyl]-3-methoxybenzoate (0.53 g) in dioxane (3 ml) was treated with triethylamine (0.31 ml) and trimethylsilyl trifluoromethanesulfonate (0.38 ml). The solution was heated under nitrogen at reflux for thirty minutes, allowed to cool, and then diluted with water to give a precipitate which was collected by filtration and dried under vacuum to give 4-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(N,N-dimethylcarbamoyl)propyl]indol-1-ylmethyl]-3-methoxybenzoic acid (0.33 g, 66%) as a yellow powder; mp 120°-122°; partial NMR (250 MHz, DMSO-d6): 1.04(d, 3H, CHCH3), 2.07-2.24(m, 1H, CH3CH), 2.71(s, 3H, NCH3), 2.80(s, 3H, NCH3), 3.93(s, 3H, OCH3), 5.42(s, 2H, NCH2), 6.58(d, 1H, Ar), 7.30(s, 1H, H2 -indole), 7.40(d, 1H, H5 -indole), 7.90(br s, 1H, H7 -indole), 8.33(br t, 1H, NH).

Workup

  1. temperatureThe solution was heated under nitrogen
  2. temperatureat reflux for thirty minutes
  3. temperatureto cool
  4. customto give a precipitate which
  5. filtrationwas collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6167556950d042a6bf547a39108ed05c
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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