1,2-Dichloroethane → 3-(azidomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

HRID 655911Notes

Reaction equation

HRID 655911 reaction equation
[N:1]([CH2:4][C:5]1[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([OH:17])=O)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:2]=[N-:3].C1C=C2N=NN(O)C2=CC=1.O.CN1CCOCC1.C(Cl)CCl.[C:46]1([C@@H:52]([NH2:55])[CH2:53][CH3:54])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>O1CCCC1>[N:1]([CH2:4][C:5]1[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([NH:55][C@H:52]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:53][CH3:54])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:2]=[N-:3]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 6993773(1S)-1-phenylpropan-1-amineHCID 578935673-(Azidomethyl)-2-phenylquinoline-4-carboxylic acid

Product 1

HCID 578935703-(azidomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamideYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(azidomethy)-2-phenylquinoline-4-carboxylic acid (2c) (997 mg, 3.28 mmol), HOBT hydrate (760 mg, 4.92 mmol), 4-methylmorpholine (551 μL, 4.92 mmol) in tetrahydrofuran (50 mL) was added EDC (960 mg, 4.92 mmol) at RT under N2. (S)-1-Phenyl propylamine (488.5 mg, 3.62 mmol) was then added and the reaction mixture stirred at RT for 12 h. All solvent was removed in vacuo and the residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution, dried over sodium sulfate and then concentrated in vacuo. The residue was purified by chromatography eluting with 15-25% ethyl acetate/hexane to give the title compound (1000 mg, 73%) as a light-yellow solid. 1H NMR (300 MHz, CDCl3) δ 0.94 (t, 3H), 2.01 (m, 2H), 5.17 (q, 1H), 5.19 (s, 2H), 5.72 (b, 1H), 7.21 (d, 2H), 7.34 (d, 2H), 7.39 (m, 1H), 7.78 (m, 2H), 7.84 (m, 2H), 8.08 (m, 1H), 8.30 (m, 2H), 8.49 (m, 2H). MS APCI, m/z=422 (M+1). LCMS: 2.47 min.

Workup

  1. customAll solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography
  6. washeluting with 15-25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2fb9b0e30e3141d9be927839528ba8e4
Source dataset
uspto-grants-2011_12
Patent number
US08071621B2

Reaction notes

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