Methanesulfonyl chloride → N-(2-(Morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide

HRID 2044099노트

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HRID 2044099 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17]>N1C=CC=CC=1>[N:18]1([C:16]([C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=2[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[O:17])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 60181686(2-Amino-4-nitrophenyl)(morpholin-4-yl)methanone

생성물 1

HCID 66833433N-(2-(Morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide수율 14.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Methanesulfonyl chloride (0.179 mL, 2.302 mmol) was added to a solution of (2-amino-4-nitrophenyl)(morpholino)methanone (0.5783 g, 2.302 mmol) in pyridine (3 mL) at 0° C. After 30 min at 0° C., the pyridine solvent was evaporated under reduced pressure. The resulting brown oil was triturated with hot CH2Cl2 and filtered. The filtrate was concentrated and purified by silica gel chromatography, eluting with 30-100% EtOAc in hexanes, to give the expected product as yellow solid (108 mg, 14% yield). LCMS: (M+H)+=330.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.83 (1H, s), 8.24 (1H, d, J=2.26 Hz), 8.07 (1H, dd, J=8.41, 1.88 Hz), 7.61 (1 H, d, J=8.53 Hz), 3.69 (2H, d, J=4.02 Hz), 3.61 (2H, br. s.), 3.57 (2H, d, J=4.27 Hz), 3.16-3.22 (2H, m), 3.10 (3H, s).

후처리

  1. customthe pyridine solvent was evaporated under reduced pressure
  2. customThe resulting brown oil was triturated with hot CH2Cl2
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel chromatography
  6. washeluting with 30-100% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-c0fe81b619874200aa934a5a47c5ead1
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586751B2

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