Triethylamine → HCID 10225541, compound

HRID 1839172Notes

Reaction equation

HRID 1839172 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9](Cl)=[O:10])[O:4][N:3]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[CH2:22][NH:23][C:24]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27]1)=[O:25].C(N(CC)CC)C>>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][NH:23][C:24]([N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27]2)=[O:25])=[O:10])[O:4][N:3]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 234501162-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoyl chlorideHCID 68761676HCID 68761676, compound

Product 1

HCID 10225541HCID 10225541, compoundYield 50%

Procedure

2-(3-Methyl-1,2,4-oxadiazol-5-yl)-benzoyl chloride (0.045 g, 0.2 mmol) in MDC (2.7 ml) was added to a solution of 2,3-dihydroindole-1-carboxylic acid (piperidin-2-ylmethyl) amide (0.05 g, 0.193 mmol) and triethylamine (0.1 ml, 0.72 mmol) in MDC (3 ml). After 20 h the reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (8 ml). The organic layer was added directly onto a dry 10 g pre-packed silica gel cartridge and eluted with 10-100% ethyl acetate in hexane gradient to afford the title compound as a colourless solid (0.043 g, 50%). Mass Spectrum (API+): Found 446 (MH+). C25H27N5O3 requires 445.

Workup

  1. washAfter 20 h the reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (8 ml)
  2. additionThe organic layer was added directly onto a dry 10 g pre-packed silica gel cartridge
  3. washeluted with 10-100% ethyl acetate in hexane gradient

Sources & evidence

ORD record
ord-ac0c0cfcbf9047fa9553c4fc46a0b47b
Source dataset
uspto-grants-2004_01
Patent number
US06677354B2

Reaction notes

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