2-Bromo-1-(3,4,5-trimethoxyphenyl)ethanone → N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-{[2-oxo-2-(3,4,5-trimethoxyphenyl)ethyl]thio}-1H-benzimidazole-5-carboxamide

HRID 883686Notes

Reaction equation

HRID 883686 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=1)=[O:4].[CH2:17]([N:21]([CH2:47][CH:48]([CH3:50])[CH3:49])[C:22]([C:24]1[CH:46]=[CH:45][C:27]2[N:28]([CH2:32][CH2:33][CH2:34][N:35]([CH3:44])[CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)[C:29](=[S:31])[NH:30][C:26]=2[CH:25]=1)=[O:23])[CH:18]([CH3:20])[CH3:19]>O1CCCC1>[CH2:47]([N:21]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:22]([C:24]1[CH:46]=[CH:45][C:27]2[N:28]([CH2:32][CH2:33][CH2:34][N:35]([CH3:44])[CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)[C:29]([S:31][CH2:2][C:3](=[O:4])[C:5]3[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=3)=[N:30][C:26]=2[CH:25]=1)=[O:23])[CH:48]([CH3:49])[CH3:50]

Participants

4

Reactant 2

HCID 36857322-Bromo-1-(3,4,5-trimethoxyphenyl)ethanoneHCID 86596757N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-thioxo-2,3-dihydro-1H-benzimidazole-5-carboxamide

Product 1

HCID 57567654N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-{[2-oxo-2-(3,4,5-trimethoxyphenyl)ethyl]thio}-1H-benzimidazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

Morpholinomethylpolystyrene resin (acquired from Novabiochem, 2 eq) and 2-bromo-1-(3,4,5-trimethoxyphenyl)ethanone are added successively to a solution of N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-thioxo-2,3-dihydro-1H-benzimidazole-5-carboxamide in tetrahydrofuran. The mixture is stirred for 15 hours at approximately 20° C. then tetrahydrofuran, aminomethylpoystyrene resin (2 eq, acquired from Novabiochem) and 4-bromomethylphenoxymethyl-polystyrene resin (3 eq, acquired from Novabiochem) are added. After stirring for 6 hours, the mixture is filtered on frit. The filtrate is then concentrated to dryness under reduced pressure at 40° C. in order to produce the expected compound.

Workup

  1. stirringAfter stirring for 6 hours
  2. filtrationthe mixture is filtered on frit
  3. concentrationThe filtrate is then concentrated to dryness under reduced pressure at 40° C. in order

Sources & evidence

ORD record
ord-07a5b66caafe4c18b80d7d4e3a8c15f1
Source dataset
uspto-grants-2012_08
Patent number
US08236965B2

Reaction notes

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