Triethylamine → methyl 2-[(3-bromobenzyl)thio]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylate

HRID 883692Notes

Reaction equation

HRID 883692 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]Br.[CH3:17][N:18]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1)[CH2:19][CH2:20][CH2:21][N:22]1[C:26]2[CH:27]=[CH:28][C:29]([C:31]([O:33][CH3:34])=[O:32])=[CH:30][C:25]=2[NH:24][C:23]1=[S:35]>O1CCCC1.C(OCC)(=O)C.O>[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][S:35][C:23]1[N:22]([CH2:21][CH2:20][CH2:19][N:18]([CH3:17])[CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)[C:26]2[CH:27]=[CH:28][C:29]([C:31]([O:33][CH3:34])=[O:32])=[CH:30][C:25]=2[N:24]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 699793-Bromobenzyl bromideHCID 86596758methyl 1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-thioxo-2,3-dihydro-1H-benzimidazole-5-carboxylate

Product 1

HCID 69026672methyl 2-[(3-bromobenzyl)thio]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylateYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Triethylamine (0.82 ml, 1.6 eq) and 3-bromobenzylbromide (0.97 g, 1 eq) are added successively to a solution of methyl 1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-thioxo-2,3-dihydro-1H-benzimidazole-5-carboxylate (1.5 g) in tetrahydrofuran (30 ml). The mixture is stirred for 15 hours at approximately 20° C. then concentrated under reduced pressure at 40° C. The residue obtained is diluted in ethyl acetate and water. After decanting and extracting, the organic phases are washed with salt water, dried over sodium sulphate and concentrated under reduced pressure at 40° C. Purification by flash chromatography on silica gel (eluent: dichloromethane/methanol 95/5 to 90/10) produces the expected compound in the form of a colourless oil (1.5 g; 70% yield).

Workup

  1. concentrationthen concentrated under reduced pressure at 40° C
  2. customThe residue obtained
  3. customAfter decanting
  4. extractionextracting
  5. washthe organic phases are washed with salt water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure at 40° C
  8. customPurification by flash chromatography on silica gel (eluent: dichloromethane/methanol 95/5 to 90/10)

Sources & evidence

ORD record
ord-04187b5f56c649a4b7fcfb9544d9b5a1
Source dataset
uspto-grants-2012_08
Patent number
US08236965B2

Reaction notes

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