Methylamine → Methyl-3-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide

HRID 2116789노트

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HRID 2116789 반응식
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([S:11][C:12]3[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=3[C:14](O)=O)=[CH:7][CH:8]=2)[NH:3]1.C[N:22]([C:24]([O:28]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN.C1COCC1>CN(C=O)C>[CH3:14][C:13]1[C:12]([S:11][C:6]2[CH:5]=[C:4]3[C:9]([CH2:10][C:2](=[O:1])[NH:3]3)=[CH:8][CH:7]=2)=[CH:20][CH:19]=[CH:18][C:17]=1[C:24]([NH2:22])=[O:28]

참가 물질

6

반응물 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 587957452-[(2-Oxo-2,3-dihydro-1H-indol-6-yl)sulfanyl]benzoic acid

생성물 1

HCID 69128281Methyl-3-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide수율 31%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(2-Oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzoic acid (as prepared in Preparation 2; 0.228 g, 0.77 mmol) was dissolved in DMF (3 mL). The resulting solution was treated with HATU (0.434 g, 1.16 mmol) and 2M MeNH2 in THF (2.68 mL, 5.36 mmol) then allowed to stir for 3 hours at room temperature. The reaction mixture was then concentrated in vacuo and the crude was re-dissolved in EtOAc (15 mL) and washed with brine (3×15 mL). The combined organics were then dried over Na2SO4, filtered and concentrated in vacuo. The crude mixture was then purified via flash silica gel chromatography (5% MeOH in CHCl3) affording the title compound as a white solid in 31% yield (71 mg, 0.239 mmol).

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe crude was re-dissolved in EtOAc (15 mL)
  3. washwashed with brine (3×15 mL)
  4. dry with materialThe combined organics were then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was then purified via flash silica gel chromatography (5% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-8e625ed69bd64a2584f1bf12e8ccb848
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439371B2

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