Methylamine → HCID 86656741, compound

HRID 452149Notes

Reaction equation

HRID 452149 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:29]=[CH:28][C:15]3/[C:16](=[CH:25]/[C:26]#[N:27])/[C:17]4[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=4[CH2:19][CH2:20][C:14]=3[CH:13]=2)[C:9]2[CH:30]=[C:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:32]=[C:33]([CH3:34])[C:8]=2[N:7]=1)(O)=[O:2].[CH2:41]([N:43]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN.C(=O)([O-])O.[Na+]>CN(C=O)C.O>[CH3:41][NH:43][C:1]([CH2:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:29]=[CH:28][C:15]3/[C:16](=[CH:25]/[C:26]#[N:27])/[C:17]4[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=4[CH2:19][CH2:20][C:14]=3[CH:13]=2)[C:9]2[CH:30]=[C:31]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:32]=[C:33]([CH3:34])[C:8]=2[N:7]=1)=[O:2]

Participants

8

Reactant 5

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 67211111HCID 67211111, compound

Product 1

HCID 86656741HCID 86656741, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

[step 1] (E)-{2-[2-(2-Carboxyethyl)-4-methyl-6-phenylbenzimidazol-1-yl]methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene}acetonitrile (100 mg, 0.19 mmol) obtained in Example 62, step 1 was dissolved in DMF (1 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (527 mg, 2.75 mmol), 1-hydroxybenzotriazole (421 mg, 2.75 mmol) and methylamine (2 mol/L THF solution; 0.38 mL, 0.72 mmol) were added, and the mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium hydrogen carbonate solution and water were added to the mixture, and the precipitated solid was collected by filtration to give (E)-{2-[2-(methylcarbamoylethyl)-4-methyl-6-phenylbenzimidazol-1-yl]methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene}acetonitrile (102 mg, 100%).

Workup

  1. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-03df64c2f1c848c484ccc9bc1d82a0cd
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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