Diisopropylethylamine → (S)-2-amino-5-bromo-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

HRID 391564

반응식

HRID 391564 반응식
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)C(C)C)(C)C.[CH3:21][S@:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[NH:24])=[O:23].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([N:24]=[S@@:22]([CH3:21])(=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:6]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7374452-Amino-5-bromonicotinic acidHCID 25036288(S)-(+)-S-Methyl-S-phenylsulfoximine

생성물 1

HCID 86629471(S)-2-amino-5-bromo-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide수율 84.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

To a solution of 2-amino-5-bromonicotinic acid (189 mg, 0.87 mmol), N,N-diisopropylethylamine (0.30 mL, 1.7 mmol), and (S)-(+)-S-methyl-S-phenylsulfoximine (162 mg, 1.0 mmol) in 4.0 mL DMF at room temperature was added BOP (423 mg, 0.96 mmol). The solution was stirred 30 minutes, then heated at 60° C. for 30 minutes, and then cooled back to room temperature. After 19 hours, the mixture was dissolved in EtOAc, washed with Na2CO3 solution, H2O, brine, dried with anhydrous Na2SO4 and rotary evaporated. The yellow foam was purified by chromatography (silica gel, CHCl3/EtOAc) to give the title compound as a light yellow solid (260 mg, 84%).

후처리

  1. temperaturecooled back to room temperature
  2. waitAfter 19 hours
  3. washwashed with Na2CO3 solution, H2O, brine
  4. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  5. customThe yellow foam was purified by chromatography (silica gel, CHCl3/EtOAc)

출처 및 근거

ORD 기록
ord-11d1990c21c843c8a25147bc2b01bb49
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383825B2

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