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

HRID 2116789ノート

反応式

HRID 2116789 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(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).

後処理

  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)

出典と根拠

ORDレコード
ord-8e625ed69bd64a2584f1bf12e8ccb848
出典データセット
uspto-grants-2008_10
特許番号
US07439371B2

反応ノート

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