Carbonate Ion → HCID 58592832, compound

HRID 642889Notes

Reaction equation

HRID 642889 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]5[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[C:29](F)[CH:28]=5)[CH2:22][CH2:21]4)[C:13]=3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:38][O:39][C:40](=[O:43])[CH2:41][NH2:42].C(=O)([O-])[O-]>CN(C)C=O>[CH3:38][O:39][C:40](=[O:43])[CH2:41][NH:42][C:29]1[CH:28]=[C:27]([CH2:26][N:23]2[CH2:22][CH2:21][N:20]([C:19]3[C:13]4[N:12]=[C:11]([C:8]5[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=5)[NH:15][C:14]=4[CH:16]=[CH:17][CH:18]=3)[CH2:25][CH2:24]2)[CH:32]=[CH:31][C:30]=1[N+:33]([O-:35])=[O:34]

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 122755Glycine methyl ester hydrochlorideHCID 585927062-(4-tert-Butyl-phenyl)-4-[4-(3-fluoro-4-nitro-benzyl)-piperazin-1-yl]-1H-benzoimidazole

Product 1

HCID 58592832HCID 58592832, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-tert-Butyl-phenyl)-4-[4-(3-fluoro-4-nitro-benzyl)-piperazin-1-yl]-1H-benzoimidazole (0.50 g, 1.03 mMol) in dimethylformamide (20 mL) was added glycine methyl ester hydrochloride (0.515 g, 4.10 mMol) and the reaction stirred at room temperature. To the homogeneous solution was added Argonaut MP carbonate resin (2.01 g, 3.06 mMol/g) and the mixture stirred for three hours. The mixture was filtered to remove the resin and the filtrate was then heated to sixty degrees and stirred overnight. Upon arrival the solution was cooled to room temperature and diluted with ethyl acetate (150 mL). After washing with water (3×50 mL) and brine (50 mL) the organics were dried with magnesium sulfate, filtered, and concentrated on a rotary evaporator. Purification by flash column chromatography on silica gel using 20 to 25% ethyl acetate in dichloromethane as eluant yielded 470 mg (82% yield) of (5-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-2-nitro-phenylamino)-acetic acid methyl ester as a yellow-orange solid. 1H NMR (DMSO-d6): δ=12.69 (s, 1H), 8.43 (t, 1H, J=4 Hz), 8.04 (d, 2H, J=8.6 Hz), 7.76 (d, 1H, J=8.3 Hz), 7.55 (d, 2H, J=8.3 Hz), 7.03 (m, 2H), 6.90 (s, 1H), 6.78 (dd, 1H, J=8.8, 1.4 Hz), 6.50 (dd, 1H, J=7.1, 1.7 Hz), 4.32 (d, 2H, J=5.8 Hz), 3.72 (s, 3H), 3.58 (m, 6H), 2.64 (br s, 4H), 1.33 (s, 9H). LC/MS (Method A), rt=1.23 mins., purity=75.0%, calculated mass=556, [M+2H]+2/2=279, [M−H]−=555.

Workup

  1. stirringthe mixture stirred for three hours
  2. filtrationThe mixture was filtered
  3. customto remove the resin
  4. temperaturethe filtrate was then heated to sixty degrees
  5. stirringstirred overnight
  6. temperatureUpon arrival the solution was cooled to room temperature
  7. additiondiluted with ethyl acetate (150 mL)
  8. washAfter washing with water (3×50 mL) and brine (50 mL) the
  9. dry with materialorganics were dried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated on a rotary evaporator
  12. customPurification by flash column chromatography on silica gel using 20 to 25% ethyl acetate in dichloromethane as eluant

Sources & evidence

ORD record
ord-c22594afb7894e0798db2f5355e7dd1b
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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