2-tert-Butyl-1,1,3,3-tetramethylguanidine → 3-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-N,N-dimethylbenzamide

HRID 706678Notes

Reaction equation

HRID 706678 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C(N=C(N(C)C)N(C)C)(C)(C)C.Cl[CH2:27][C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=1)[C:31]([N:33]([CH3:35])[CH3:34])=[O:32]>CC#N>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:27][C:28]2[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=2)[C:31]([N:33]([CH3:35])[CH3:34])=[O:32])[N:3]=1

Participants

5

Reactant 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 218746043-(chloromethyl)-N,N-dimethylbenzamideHCID 178526562HCID 178526562, compound

Product 1

HCID 679762773-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-N,N-dimethylbenzamideYield 72.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a flask was added 3-iodo-4-nitro-1H-indazole (0.500 g, 1.73 mmol) and CH3CN (6 mL) followed by 2-tert-butyl-1,1,3,3-tetramethylguanidine (0.523 ml, 2.59 mmol). The mixture was stirred for 5 minutes, and then 3-(chloromethyl)-N,N-dimethylbenzamide (0.479 g, 2.42 mmol) was added as a CH3CN (4 mL) solution. The reaction was stirred at ambient temperature for 5 hours. The mixture was concentrated and diluted with saturated aqueous NH4Cl (20 mL) and EtOAc (60 mL). The layers were mixed and separated and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (EtOAc) to provide 0.567 g (72%) of the desired product as an orange foam.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 5 hours
  2. concentrationThe mixture was concentrated
  3. additiondiluted with saturated aqueous NH4Cl (20 mL) and EtOAc (60 mL)
  4. additionThe layers were mixed
  5. customseparated
  6. washthe organic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-a6d5d912a75a4aa3a85f8d655e47c6b0
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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