1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67210808, compound

HRID 452160Notes

Reaction equation

HRID 452160 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].[OH:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C=O)C>[OH:36][CH:37]1[CH2:42][CH2:41][N:40]([C:26]([C:25]2[C:20]3[N:19]=[C:18]([CH2:29][CH2:30][CH3:31])[N:17]([CH2:16][C:14]4[CH:13]=[CH:12][C:11]5/[C:5](=[C:3](/[CH3:4])\[C:1]#[N:2])/[C:6]6[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=6[O:8][CH2:9][C:10]=5[CH:15]=4)[C:21]=3[CH:22]=[CH:23][CH:24]=2)=[O:27])[CH2:39][CH2:38]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 79341Piperidin-4-olHCID 516892Sodium BicarbonateHCID 67210872HCID 67210872, compound

Product 1

HCID 67210808HCID 67210808, compoundYield 100%

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), 4-hydroxypiperidine (96 mg, 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 93/7) to give (E)-2-{8-[4-(4-hydroxy-1-piperidinecarbonyl)-2-propylbenzimidazol-1-yl]methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene}propiononitrile (260 mg, 100%). [step 2] Using (E)-2-{8-[4-(4-hydroxy-1-piperidinecarbonyl)-2-propylbenzimidazol-1-yl]methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene}propiononitrile (260 mg, 0.48 mmol) obtained in step 1 and in the same manner as in Example 5, the title compound (compound 101) (85 mg, 30%) 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 93/7)

Sources & evidence

ORD record
ord-0c65f884b7744171be7ac091483b2e49
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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