Triethylamine → HCID 67082857, compound

HRID 1944512Notes

Reaction equation

HRID 1944512 reaction equation
CC(C1C=[CH:11][C:10]([CH2:13][CH2:14][C:15]([NH:17][C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:16])=CC=1)CCCC.[CH3:28][CH:29]([C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=O)=[CH:36][CH:35]=1)[CH2:30][CH2:31][CH2:32][CH3:33].[CH3:43]CN(CC)CC.NC1C=NC2C(C=1)=CC=CC=2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH3:28][CH:29]([C:34]1[CH:42]=[CH:41][C:37]([C:38]2[CH:43]=[C:14]([CH:13]=[CH:10][CH:11]=2)[C:15]([NH:17][C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:16])=[CH:36][CH:35]=1)[CH2:30][CH2:31][CH2:32][CH3:33]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 113753-AminoquinolineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10451174HCID 10451174, compoundHCID 59859900HCID 59859900, compound

Product 1

HCID 67082857HCID 67082857, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[4-(1-Methyl-pentyl)-phenyl]-N-quinolin-3-yl-propionamide. 4-(1-Methyl-pentyl)-benzoic acid from step B (0.114 g, 0.55 mmol) was dissolved in 5 mL DMF with stirring. To this was added Et3N (0.10 mL, 0.72 mmol), 3-aminoquinoline (0.082 g, 0.57 mmol) and lastly HBTU (0.224 g, 0.59 mmol). The reaction was allowed to stir overnight then poured into 25 mL EtOAc and washed with saturated NaHCO3 solution (25 mL) then brine (25 mL). The organics were dried over Na2SO4, filtered, evaporated in vacuo and the residue chromatographed over silica gel eluting with 0% to 40% EtOAc in hexanes. Evaporation of the proper fractions yielded the title product (0.120 g, 0.36 mmol). 1H NMR (DMSO-d6): 8.93 (d, 1H), 8.86 (d, 1H), 8.09 (m, 2H), 7.88 (m, 3H), 7.67 (dt, 1H), 7.57 (t, 1H), 7.35 (d, 2H), 2.79 (h, 1H), 1.61 (q, 2H), 1.37-1.04 (m, 7H), 0.87 (t, 3H); MS: m/z 333.4 (MH+).

Workup

  1. stirringto stir overnight
  2. washwashed with saturated NaHCO3 solution (25 mL)
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customthe residue chromatographed over silica gel eluting with 0% to 40% EtOAc in hexanes
  7. customEvaporation of the proper fractions

Sources & evidence

ORD record
ord-fde26156a63e4b03bf72bc82748b9ef9
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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