Benzoylhydrazine → N'-benzoyl-3-iodo-1-tosyl-1H-indole-5-carbohydrazide

HRID 634237Notes

Reaction equation

HRID 634237 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11](O)=[O:12])[CH:9]=2)[N:4]([S:14]([C:17]2[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1.[C:24]([NH:32][NH2:33])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[C:24]([NH:32][NH:33][C:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH:3]=[C:2]2[I:1])=[O:12])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 11955BenzoylhydrazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 683285993-iodo-1-tosyl-1H-indole-5-carboxylic acid

Product 1

HCID 68328452N'-benzoyl-3-iodo-1-tosyl-1H-indole-5-carbohydrazideYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring suspension of 3-iodo-1-tosyl-1H-indole-5-carboxylic acid (515 mg, 1.17 mmol) and benzohydrazide (159 mg, 1.167 mmol) in THF (10 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.51 mL, 2.92 mmol) followed by HATU (488 mg, 1.28 mmol) in one portion and the solution was stirred at RT for 2 h. The reaction was quenched with 20 mL of ice cold H2O and extracted with EtOAc (2×50 mL). The organic layer was washed with 10 mL of sat. NaHCO3 followed by brine, and dried over Na2SO4. It was concentrated to about 5 mL and the precipitated solid was filtered, rinsed with EtOAc (2×2 mL). The white solid was collected and dried in a vacuum oven for 5 h at 40° C. affording N′-benzoyl-3-iodo-1-tosyl-1H-indole-5-carbohydrazide (305 mg, 47%) as an off-white crystalline solid. MS (ESI, pos. ion) m/z: 560.0 (M+1). 1H NMR (400 MHz, DMSO-D6) δ ppm 10.67 (1H, s), 10.52 (1H, s), 8.19 (1H, s), 8.08 (1H, d, J=8.4 Hz), 78.03-7.88 (6H, m), 7.67-7.49 (3H, m), 7.42 (2H, d, J=8.2 Hz), 2.33 (3H, s).

Workup

  1. customThe reaction was quenched with 20 mL of ice cold H2O
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe organic layer was washed with 10 mL of sat. NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationIt was concentrated to about 5 mL
  6. filtrationthe precipitated solid was filtered
  7. washrinsed with EtOAc (2×2 mL)
  8. customThe white solid was collected
  9. customdried in a vacuum oven for 5 h at 40° C.

Sources & evidence

ORD record
ord-29a1476d1ed14f2da15d63cee689cc1c
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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