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2-(Di-tert-butylphosphino)biphenyl → (S)-2-sec-Butylamino-6-(cyclopropanesulfonyl-methylamino)-isonicotinic acid methyl ester

HRID 1436530
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HRID 1436530 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[CH:5]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[CH3:38][NH:39][S:40]([CH:43]1[CH2:45][CH2:44]1)(=[O:42])=[O:41].[Na]>C1(C)C=CC=CC=1.C1COCC1.C(OCC)(=O)C.C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([N:39]([S:40]([CH:43]2[CH2:45][CH2:44]2)(=[O:42])=[O:41])[CH3:38])[N:7]=[C:6]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[CH:5]=1
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참가 물질

9

반응물 3

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 68815009Sodium cyclopropanesulfonic acid methylamideHCID 86614996HCID 86614996, 화합물

생성물 1

HCID 68815532(S)-2-sec-Butylamino-6-(cyclopropanesulfonyl-methylamino)-isonicotinic acid methyl ester

시약·촉매·용매 5

HCID 9811564Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매
HCID 3283Diethyl Ether용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

Dissolve (S)-2-sec-butylamino-6-chloro-isonicotinic acid methyl ester (880 mg, 3.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (164 mg, 0.18 mmol), 2-(di-tert-butylphosphino)biphenyl (107 mg, 0.36 mmol) in toluene (18 mL) and THF (2 mL) in a previously nitrogen-filled sealed vessel. Add sodium cyclopropanesulfonic acid methylamide (700 mg, 4.42 mmol) into the mixture under nitrogen and flush the reactants again with nitrogen before sealing and heating overnight at 100° C. Cool the reaction to room temperature and dilute with ethyl acetate and diethyl ether and filter through a filtering agent. Concentrate and purify (silica gel chromatography, eluting with 0:100 to 08:92 ethyl acetate:hexanes) to give the title compound.

후처리

  1. additionfilled
  2. customsealed vessel
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationfilter through a filtering agent
  6. concentrationConcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 0:100 to 08:92 ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-765f9563881148ac8bf7f81f8e5b50c6
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07618978B2

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