Sodium Hydroxide → 2-Methyl-7-(2,4,6-trimethyl-phenyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid cyclopropylmethyl-propyl-amide

HRID 1295838Notes

Reaction equation

HRID 1295838 reaction equation
C[Al](C)C.[CH:5]1([CH2:8][NH:9][CH2:10][CH2:11][CH3:12])[CH2:7][CH2:6]1.C(O[C:16]([C:18]1[N:22]2[CH2:23][CH2:24][N:25]([C:26]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=3[CH3:34])[C:21]2=[N:20][C:19]=1[CH3:35])=[O:17])C.[OH-].[Na+]>C1C=CC=CC=1>[CH:5]1([CH2:8][N:9]([CH2:10][CH2:11][CH3:12])[C:16]([C:18]2[N:22]3[CH2:23][CH2:24][N:25]([C:26]4[C:27]([CH3:34])=[CH:28][C:29]([CH3:33])=[CH:30][C:31]=4[CH3:32])[C:21]3=[N:20][C:19]=2[CH3:35])=[O:17])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 117787Cyclopropanemethanamine, N-propyl-HCID 16682925TrimethylaluminumHCID 20780238HCID 20780238, compound

Product 1

HCID 207802822-Methyl-7-(2,4,6-trimethyl-phenyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid cyclopropylmethyl-propyl-amideYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of trimethyl aluminum (2.0 M in heptane, 2.2 mL, 4.4 mmol) was added to a solution of N-cyclopropylmethyl-N-propylamine (0.63 mL, 4.4 mmol) in benzene (3 mL) at 0° C. The mixture was warmed up to room temperature and stirred at this temperature for 1.5 h, and then added to a stirred solution of 2-methyl-7-(2,4,6-trimethyl-phenyl)-6,7-dihydro-5H-imidazo[1,2-α]imidazole-3-carboxylic acid ethyl ester (0.172 g, 0.55 mmol) in benzene (8.0 mL). The mixture was refluxed for 12 h. Upon cooling at 0° C., 1 N sodium hydroxide (25 mL) was added dropwise to the above mixture. The mixture was extracted with dicholoromethane (40 mL), and the organic layer was dried over anhydrous sodium sulfate. Solvents were removed in vacuo and the residue was subjected to chromatography using ethyl acetate/hexanes (1:1) as eluent to afford the title compound as a light yellow oil which solidified upon cooling (0.209 g, 100% yield). 1H NMR (CDCl3, 300 MHz) δ; 13C NMR (CDCl3, 75 MHz) δ 163.1, 156.0, 141.0, 136.5, 136.1, 132.7, 128.7, 115.8, 52.6, 50.3, 47.1, 42.1, 20.1, 19.9, 17.3, 14.6, 10.3, 9.2, 2.8. Mass spec.: 381.26 (MH+).

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. temperatureUpon cooling at 0° C.
  3. extractionThe mixture was extracted with dicholoromethane (40 mL)
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-91750907196845a0960442183c4cd4ed
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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