Water → HCID 59853933, compound

HRID 2061237Notes

Reaction equation

HRID 2061237 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:21][CH2:20][N:19]([C:22]([NH:24][CH2:25][C:26]([OH:28])=O)=[O:23])[CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:29]([NH2:33])([CH3:32])([CH3:31])[CH3:30].Cl.C(N=C=NCCCN(C)C)C.O>ClCCl>[C:29]([NH:33][C:26](=[O:28])[CH2:25][NH:24][C:22]([N:19]1[CH2:18][CH2:17][C:16](=[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)[CH2:21][CH2:20]1)=[O:23])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6385Tert-ButylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68420356HCID 68420356, compound

Product 1

HCID 59853933HCID 59853933, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

300 mg (0.801 mmol) of ({[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]carbonyl}amino)acetic acid, 1.0 ml (0.961 mmol) of t-butylamine and 230 mg (1.20 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride were dissolved in 10 ml of dichloromethane. The obtained solution was stirred at room temperature for 1 hour. Water was added to the reaction mixture. After extracting with dichloromethane, the dichloromethane layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue thus obtained was purified by the silica gel chromatography (dichloromethane:methanol=4:1 to 1:9) to obtain the title compound.

Workup

  1. extractionAfter extracting with dichloromethane
  2. dry with materialthe dichloromethane layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by the silica gel chromatography (dichloromethane:methanol=4:1 to 1:9)

Sources & evidence

ORD record
ord-be7ac9aa7c6e4489ab688e0ab9d74f09
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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