1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3,5-Dimethoxy-4-methyl-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitro-benzyl]-benzamide

HRID 1296738Notes

Reaction equation

HRID 1296738 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[C:9]([N+:15]([O-:17])=[O:16])[CH:8]=2)[N:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([O:30][CH3:31])[C:28]=1[CH3:29])[C:23](O)=[O:24].CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>ClCCl.CN(C=O)C.C(OCC)(=O)C>[CH3:31][O:30][C:27]1[CH:26]=[C:22]([CH:21]=[C:20]([O:19][CH3:18])[C:28]=1[CH3:29])[C:23]([NH:12][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([C:4]2[N:3]=[C:2]([CH3:1])[O:6][N:5]=2)=[CH:8][C:9]=1[N+:15]([O-:17])=[O:16])=[O:24]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 37644863,5-Dimethoxy-4-methylbenzoic acidHCID 694915744-(5-Methyl-[1,2,4]oxadiazol-3-yl)-2-nitro-benzylamine

Product 1

HCID 694895423,5-Dimethoxy-4-methyl-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitro-benzyl]-benzamideYield 94.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of compound 1e (3.34 g, 14.3 mmol), 3,5-dimethoxy-4-methylbenzoic acid (4.2 g, 21.4 mmol), EDCI (4.1 g, 21.4 mmol), and HOAt (190 mg, 1.4 mmol) in a mixture of dichloromethane (60 mL) and DMF (30 mL) was stirred at rt for 12 h. The reaction mixture was diluted with ethyl acetate and washed with 1 N HCl. The solid which precipitated was recovered by filtration. The ethyl acetate layer was washed with saturated NaHCO3 solution and brine, dried Na2SO4, and concentrated on a rotary evaporator. The residue was recrystallized (ethyl acetate/hexane/petroleum ether) and combined with the filtered solid to afford compound 1f (5.55 g, 94%) as a cream colored solid. ESI-MS m/e 413.2 (M+1).

Workup

  1. washwashed with 1 N HCl
  2. customThe solid which precipitated
  3. filtrationwas recovered by filtration
  4. washThe ethyl acetate layer was washed with saturated NaHCO3 solution and brine, dried Na2SO4
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was recrystallized (ethyl acetate/hexane/petroleum ether)

Sources & evidence

ORD record
ord-9868a5edffc54bc3a4795a499b619956
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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