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

HRID 2425512

반응식

HRID 2425512 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d95c1573116e4c78ac3e5899f6efa0eb
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964733B2

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