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

HRID 2425512

反応式

HRID 2425512 の反応式
[CH2:1]([S:3][C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:6][C:7]2[C:12]([C:13]=1[C:14]([OH:16])=O)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2].C1C=C2N=NN(O)C2=CC=1.O.CN1CCOCC1.C(Cl)CCl.[C:45]1([C@@H:51]([NH2:54])[CH2:52][CH3:53])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(Cl)Cl>[CH2:1]([S:3][C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:6][C:7]2[C:12]([C:13]=1[C:14]([NH:54][C@H:51]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:52][CH3:53])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 6245133-(Ethylthio)-2-phenylquinoline-4-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 6993773(1S)-1-phenylpropan-1-amine

生成物 1

HCID 593234873-(ethylthio)-2-phenyl-N-[(1S)-1-phenylpropyl]quinolin-4-carboxamide収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 3-(ethylthio)-2-phenylquinoline-4-carboxylic acid (4) (269 mg, 0.87 mmol), HOBT hydrate (230 mg, 1.5 mmol), 4-methylmorpholine (164 μL, 1.5 mmol) in DCM (30 ml) was added EDC (289 mg, 1.5 mmol) at RT under N2. (S)-1-Phenyl propylamine (202 mg, 1.5 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 0.5 N HCl aqueous solution. The organic phase was washed with 10% aqueous sodium bicarbonate solution, brine, and dried over sodium sulfate. The organic solution was then concentrated in vacuo. The residue was purified by chromatography eluting with 15-25% ethyl acetate/hexane to give the title compound (315 mg, 85% yield) as a solid. 1H NMR (300 MHz, CDCl3) δ 0.96 (t, 3H), 1.22 (t, 3H), 2.0 (m, 2H), 2.40 (m, 2H), 5.28 (q, 1H), 7.20 (d, 2H), 7.34 (d, 2H), 7.39 (m, 2H), 7.78 (m, 2H), 7.84 (m, 2H), 8.00 (m, 1H), 8.11 (m, 2H), 8.15 (m, 2H). MS APCI, m/z=427 (M+1). LCMS: 2.82 min.

後処理

  1. customAll solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and 0.5 N HCl aqueous solution
  3. washThe organic phase was washed with 10% aqueous sodium bicarbonate solution, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe organic solution was then concentrated in vacuo
  6. customThe residue was purified by chromatography
  7. washeluting with 15-25% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-d95c1573116e4c78ac3e5899f6efa0eb
出典データセット
uspto-grants-2011_06
特許番号
US07964733B2

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