Sodium Carbonate → N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-[pyrimidin-2-yl]phenyl)pyridine-3-sulphonamide

HRID 1384236노트

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HRID 1384236 반응식
C(=O)([O-])[O-].[Na+].[Na+].[C:7]1(B(O)O)[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1.Cl[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.Cl[C:27]1[C:32]([S:33]([N:36]([C:46]([O:48][CH2:49][CH:50]([CH3:52])[CH3:51])=[O:47])[C:37]2[C:42]([O:43][CH3:44])=[N:41][C:40]([CH3:45])=[CH:39][N:38]=2)(=[O:35])=[O:34])=[CH:31][CH:30]=[CH:29][N:28]=1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(O)C>[CH2:49]([O:48][C:46]([N:36]([C:37]1[C:42]([O:43][CH3:44])=[N:41][C:40]([CH3:45])=[CH:39][N:38]=1)[S:33]([C:32]1[C:27]([C:7]2[CH:12]=[CH:11][C:10]([C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:9][CH:8]=2)=[N:28][CH:29]=[CH:30][CH:31]=1)(=[O:35])=[O:34])=[O:47])[CH:50]([CH3:52])[CH3:51]

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 2304781,4-Benzenediboronic acidHCID 11015197Isobutyl (2-chloropyridin-3-yl)sulfonyl(3-methoxy-5-methylpyrazin-2-yl)carbamate

생성물 1

HCID 21186320N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-[pyrimidin-2-yl]phenyl)pyridine-3-sulphonamide수율 17.9%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 1140Toluene용매

실험 절차

Tetrakis(triphenylphosphine)palladium (0) (60 mg) was added to a deoxygenated solution of sodium carbonate (233 mg), 1,4-benzenediboronic acid (165 mg), 2-chloropyrimidine (114.5 mg) and 2-chloro-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (414 mg) in a mixture of water (1.6 ml), ethanol (4 ml) and toluene (8 ml). The mixture was stirred and heated under argon under reflux for 16 hours and then allowed to cool to ambient temperature. Water (15 ml) was added and the mixture was extracted with ethyl acetate (2×20 ml). The combined organic layers were washed with saturated sodium chloride solution and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column, eluting with 25-100% ethyl acetate/hexane to give N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-[pyrimidin-2-yl]phenyl)pyridine-3-sulphonamide (95 mg) as a solid, mass spectrum (+ve ESP): 535 (M+H)+.

후처리

  1. temperatureheated under argon
  2. temperatureunder reflux for 16 hours
  3. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
  4. washThe combined organic layers were washed with saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  8. washeluting with 25-100% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-ecfcb00a066346dba3f26ebbe8a1865b
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06258817B1

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