Triethylamine → 6-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

HRID 2382961노트

반응식

HRID 2382961 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:18]([OH:20])=O)[C:5]2[CH:6]=[N:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:9]=2[CH:10]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([S:69]([NH:72][CH3:73])(=[O:71])=[O:70])=[CH:65][CH:64]=1>CN(C=O)C>[CH3:73][NH:72][S:69]([C:66]1[CH:67]=[CH:68][C:63]([CH2:62][NH:61][C:18]([C:4]2[C:5]3[CH:6]=[N:7][N:8]([C:11]4[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=4)[C:9]=3[CH:10]=[C:2]([Br:1])[CH:3]=2)=[O:20])=[CH:64][CH:65]=1)(=[O:70])=[O:71]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 164609784-(Aminomethyl)-N-methylbenzene-1-sulfonamideHCID 581389136-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

생성물 1

HCID 444698036-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred room temperature solution of 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (0.25 g, 0.70 mmol) in DMF (15 mL) was added PyBOP (0.45 g, 0.90 mmol) and triethylamine (0.20 g, 1.6 mmol). After 15 minutes, 4-aminomethyl-N-methyl-benzenesulfonamide (0.15 g, 0.7 mmol) was added. After 5 hours, the reaction was quenched with water (30 mL), and extracted with ethyl acetate (30 mL). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 30-50% ethyl acetate in hexanes to afford the title compound.

후처리

  1. waitAfter 5 hours
  2. customthe reaction was quenched with water (30 mL)
  3. extractionextracted with ethyl acetate (30 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a gradient of 30-50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-8248aabbfc4044ac8222ee255406ed80
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263597B2

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