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

HRID 2116789Notes

Reaction equation

HRID 2116789 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(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).

Workup

  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)

Sources & evidence

ORD record
ord-8e625ed69bd64a2584f1bf12e8ccb848
Source dataset
uspto-grants-2008_10
Patent number
US07439371B2

Reaction notes

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