Triethylamine → HCID 16036824, compound

HRID 2425510Notes

Reaction equation

HRID 2425510 reaction equation
[CH3:1][S:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([OH:15])=O)=[CH:10][CH:9]=[CH:8][CH:7]=2.C(N(CC)CC)C.S(Cl)(Cl)=O.[C:33]1([C@@H:39]([NH2:42])[CH2:40][CH3:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CCOC(C)=O.O>[CH3:1][S:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([NH:42][C@H:39]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:40][CH3:41])=[O:15])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 291267HCID 291267, compoundHCID 6993773(1S)-1-phenylpropan-1-amine

Product 1

HCID 16036824HCID 16036824, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 3-(methylthio)-2-phenylquinoline-4-carboxylic acid (150 mg, 0.51 mmol) and triethylamine (0.17 mL, 1.22 mmol) in EtOAc (2.5 mL) at 5° C. was added thionyl chloride (0.043 mL, 0.61 mmol). The cooling bath was removed and the suspension allowed to stir for 0.5 h, then (S)-(−)-1-phenylpropylamine (76 mg, 0.56 mmol) was added and reaction allowed to stir for another 0.5 h. Water (2 mL) and EtOAc (2 mL) were then added, the layers shaken together, then separated, the organics dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting material was purified by silica gel chromatography (0-20% EtOAc/CH2Cl2) to give the desired product (150 mg, 70% yield) as a solid. 1H NMR (300 MHz, CDCl3) δ 8.11 (d, J=8.4 Hz, 1H), 7.78-7.67 (m, 4H), 7.55-7.27 (m, 9H), 6.12 (d, J=8.5 Hz, 1H), 5.30 (q, J=7.6 Hz, 1H), 2.16-1.91 (m, 5H), 1.06 (t, J=7.4 Hz, 3H); HRMS m/z 413.1669, calcd 413.1688.

Workup

  1. customThe cooling bath was removed
  2. customreaction
  3. stirringto stir for another 0.5 h
  4. stirringthe layers shaken together
  5. customseparated
  6. dry with materialthe organics dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting material was purified by silica gel chromatography (0-20% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-93ed41bef03d491084f0783ce34c2f63
Source dataset
uspto-grants-2011_06
Patent number
US07964733B2

Reaction notes

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