Ethanolamine → HCID 67210947, compound

HRID 452161Notes

Reaction equation

HRID 452161 reaction equation
[C:1](/[C:3](=[C:5]1/[C:6]2[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=2[O:8][CH2:9][C:10]2[CH:15]=[C:14]([CH2:16][N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[C:25]([C:26](O)=[O:27])[C:20]=4[N:19]=[C:18]3[CH2:29][CH2:30][CH3:31])[CH:13]=[CH:12][C:11]/1=2)/[CH3:4])#[N:2].[NH2:36][CH2:37][CH2:38][OH:39].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C=O)C>[OH:39][CH2:38][CH2:37][NH:36][C:26]([C:25]1[C:20]2[N:19]=[C:18]([CH2:29][CH2:30][CH3:31])[N:17]([CH2:16][C:14]3[CH:13]=[CH:12][C:11]4/[C:5](=[C:3](\[C:1]#[N:2])/[CH3:4])/[C:6]5[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=5[O:8][CH2:9][C:10]=4[CH:15]=3)[C:21]=2[CH:22]=[CH:23][CH:24]=1)=[O:27]

Participants

7

Reactant 5

HCID 700EthanolamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 67210872HCID 67210872, compound

Product 1

HCID 67210947HCID 67210947, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[step 1] (E)-1-[11-(1-Cyanoethylidene)-6,11-dihydrodibenzo[b,e]oxepin-8-yl]methyl-2-propylbenzimidazole-4-carboxylic acid (220 mg, 0.48 mmol) obtained in Example 100, step 2 was dissolved in DMF (4.0 mL), 2-aminoethanol (57 μL, 0.95 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (109 mg, 0.57 mmol) and 1-hydroxybenzotriazole (87 mg, 0.57 mmol) were added, and the mixture was stirred at room temperature for 15 hr. Saturated aqueous sodium hydrogen carbonate solution (15 mL) was added to the mixture, and the precipitated solid was collected by filtration. The residue was purified by silica gel column chromatography (chloroform/methanol=99/1 to 95/5) to give (E)-N-(2-hydroxyethyl) 1-[11-(1-cyanoethylidene)-6,11-dihydrodibenzo[b,e]oxepin-8-yl]methyl-2-propylbenzimidazole-4-carboxamide (241 mg, 99%). [step 2] Using (E)-N-(2-hydroxyethyl) 1-[11-(1-cyanoethylidene)-6,11-dihydrodibenzo[b,e]oxepin-8-yl]methyl-2-propylbenzimidazole-4-carboxamide (240 mg, 0.47 mmol) obtained in step 1 and in the same manner as in Example 5, the title compound (compound 102) (70 mg, 26%) was obtained.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customThe residue was purified by silica gel column chromatography (chloroform/methanol=99/1 to 95/5)

Sources & evidence

ORD record
ord-2d4c9c8e086148b7bf55915f2e31371b
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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