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

HRID 655911ノート

反応式

HRID 655911 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2fb9b0e30e3141d9be927839528ba8e4
出典データセット
uspto-grants-2011_12
特許番号
US08071621B2

反応ノート

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