Methanol → HCID 20780214, compound

HRID 1349422Notes

Reaction equation

HRID 1349422 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([Br:12])=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2].Br[CH2:14][C:15]([NH:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26])=[O:16].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.CO>C1(C)C=CC=CC=1.CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:14][C:15](=[O:16])[NH:17][C:18]2[C:19]([CH3:26])=[CH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])[C:8]([Br:12])=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 21916126HCID 21916126, compoundHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 178470341HCID 178470341, compound

Product 1

HCID 20780214HCID 20780214, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-bromo-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester (1.00 g, 4.291 mmol) and 2-bromo-N-(2,4,6-trimethyl-phenyl)-acetamide (1.209 g, 4.720 mmol) in a mixture of toluene (16 mL) and acetone (8 mL) was added diazabicycloundecene (0.71 mL, 4.720 mmol). The resulting solution was stirred at room temperature for 24 h. Methanol (10 mL) was added to dissolve the precipitate formed, followed by the addition of silica gel (25 g). The solvent was removed under reduced pressure to dryness and the residue was applied to a silica gel-packed column. The isolation of the product was achieved by column chromatography (hexanes—ethyl acetate 4:1 to 1:2). Yield—0.736 g (42%). 1H NMR (DMSO d-6, 500 MHz) δ 9.52 (s, 1H), 6.86 (s, 2H), 5.15 (br s, 2H), 4.25 (q, J=7.1 Hz, 2H), 2.38 (s, 3H), 2.21 (s, 3H), 2.11 (s, 6H), 1.30 (t, J=7.1 Hz, 3H); LC/MS: tR=1.46 min., MS: [M+H]=408.

Workup

  1. dissolutionto dissolve the precipitate
  2. customformed
  3. additionfollowed by the addition of silica gel (25 g)
  4. customThe solvent was removed under reduced pressure to dryness

Sources & evidence

ORD record
ord-bfd4b56bcde84e2592d14c92f43d2474
Source dataset
uspto-grants-2007_05
Patent number
US07211669B2

Reaction notes

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