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Hydrochloric Acid → HCID 10326267, 화합물

HRID 853988
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HRID 853988 반응식
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]2[C:7]=1[C:8](=[O:33])[N:9]([C@@H:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][CH3:32])[CH:23]=1)[CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:10]2)=[O:4].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.Cl>CC#N.CCOCC>[Cl:15][C:12]1[CH:13]=[CH:14][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[C:7]2[C:11]=1[CH2:10][N:9]([C@@H:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][CH3:32])[CH:23]=1)[CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:8]2=[O:33]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 68690088(1S)-2-chloro-N-{7-chloro-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide

생성물 1

HCID 10326267HCID 10326267, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매
HCID 6342
Acetonitrile
용매

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온도
70 °C

실험 절차

To a solution of (1S)-2-chloro-N-{7-chloro-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (250 mg, 0.48 mmol) in CH3CN (10 ml) was added morpholine (0.17 ml, 1.94 mmol). The mixture was heated at 70° C. for 2 hrs. The reaction mixture was concentrated on rota-vap and extracted with water (50 ml) and EtOAc (50 ml). The organic layer was washed with water (50 ml), brine (25 ml), dried over Na2SO4 and concentrated. The resulted oil was purified by chromatography to give an oil which was stirred with HCl in ether (3 ml) to give (1S)-N-{7-chloro-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-2-morpholin-4-yl-acetamide; hydrochloride as a white solid (200 mg, 68% yield): mp, 198-200° C.; 1H NMR (CDCl3 with D2O added) δ 1.46 (t, J=7.0 Hz, 3H, OCH2CH3), 2.68 (broad, 4H, CH2NCH2 on morpholino ring), 2.99 (s, 3H, SCH3), 3.24 (broad, 2H, CH2NCO), 3.72 (dd, J=5, 15 Hz, 1H, CHHSO2), 3.87-3.92 (m, 7H, OCH3+CH2OCH2 on morpholine ring), 4.05-4.23 (m, 4H, CHHSO2+CNHH+OCH2CH3), 4.40 (d, J=115 Hz, 1H, CHHN), 5.71-5.77 (n, 1H, NCH), 6.86-6.97 (m, 3H, Ar), 7.40 (d, J=8 Hz, 1H, Ar), 8.52 (d, J=8 Hz, 1H, Ar); 13C NMR (CDCl3) δ 14.75, 41.71, 47.09, 51.22, 51.59, 55.09, 56.02, 63.81, 64.10, 64.81, 105.68, 111.67, 112.28, 119.32, 120.0, 120.27, 124.03, 128.81, 133.20, 134.72, 139.41, 149.09, 150.01, 168.55. Anal Calcd for C26H33Cl2N3O7S+0.53H2O: C, 51.02; H, 5.61; N, 6.87. Found: C, 50.70; H, 5.38; N, 6.76, 0.98% H2O.

후처리

  1. concentrationThe reaction mixture was concentrated on rota-vap
  2. extractionextracted with water (50 ml) and EtOAc (50 ml)
  3. washThe organic layer was washed with water (50 ml), brine (25 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulted oil was purified by chromatography
  7. customto give an oil which

출처 및 근거

ORD 기록
ord-10974fa26b484bc8997554d95793d8ee
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07256210B2

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