Ammonia → 1-(2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazol-5-yl)-3-thien-2-ylpropan-1-one

HRID 1727417Notes

Reaction equation

HRID 1727417 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([NH:23][C:24]2[N:28]([CH2:29][CH2:30][CH2:31][N:32]([CH3:41])[CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[C:27]3[CH:42]=[CH:43][C:44]([C:46](O)=[O:47])=[CH:45][C:26]=3[N:25]=2)[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1.[S:49]1[CH:53]=[CH:52][CH:51]=[C:50]1[CH2:54][CH2:55]N.N.CN=C=S>C(Cl)(Cl)Cl.CN(C)C=O.O1CCCC1.ClCCl>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([NH:23][C:24]2[N:28]([CH2:29][CH2:30][CH2:31][N:32]([CH3:41])[CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[C:27]3[CH:42]=[CH:43][C:44]([C:46](=[O:47])[CH2:55][CH2:54][C:50]4[S:49][CH:53]=[CH:52][CH:51]=4)=[CH:45][C:26]=3[N:25]=2)[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1

Participants

10

Reactant 5

HCID 222AmmoniaHCID 11167Methyl isothiocyanateHCID 682631,1'-CarbonyldiimidazoleHCID 116521ThiopheneethanamineHCID 690297442-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 690266811-(2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazol-5-yl)-3-thien-2-ylpropan-1-one

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

Carbonyldiimidazole (10.5 mg, 1.3 eq) in solution in chloroform (0.2 ml) is added to a solution of 2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylic acid (24 mg, 1 eq) in a mixture of dimethylformamide (0.2 ml) and tetrahydrofuran (0.4 ml). The mixture is stirred for 15 hours at approximately 20° C. then thiophene-2-ethylamine (13 mg, 2 eq) in solution in tetrahydrofuran (0.1 ml) is added. After stirring for 15 hours at approximately 20° C., aminomethyl polystyrene resin (2 eq), TBD-methyl polystyrene resin (2 eq) and methylisothiocyanate polystyrene resin (4 eq) are added to the mixture diluted in dichloromethane. After stirring for 6 hours at approximately 20° C., the mixture is filtered and the filtrate is concentrated under reduced pressure at 40° C. in order to produce the expected compound in the form of an oil (27 mg, 90% yield).

Workup

  1. stirringAfter stirring for 15 hours at approximately 20° C.
  2. stirringAfter stirring for 6 hours at approximately 20° C.
  3. filtrationthe mixture is filtered
  4. concentrationthe filtrate is concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record
ord-5a8c691a62f9499d89f04e306bb17569
Source dataset
uspto-grants-2009_02
Patent number
US07495110B2

Reaction notes

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