1-Hydroxybenzotriazole → [4-(4-dipropylaminomethylphenylcarbamoyl)benzyl]carbamic Acid t-butyl Ester

HRID 1173995Notes

Reaction equation

HRID 1173995 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH2:41]([N:44]([CH2:48][C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=1)[CH2:45][CH2:46][CH3:47])[CH2:42][CH3:43]>C(Cl)(Cl)Cl.CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14](=[O:16])[NH:55][C:52]2[CH:53]=[CH:54][C:49]([CH2:48][N:44]([CH2:45][CH2:46][CH3:47])[CH2:41][CH2:42][CH3:43])=[CH:50][CH:51]=2)=[CH:17][CH:18]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167770114-Dipropylaminomethyl-aniline

Product 1

HCID 66941656[4-(4-dipropylaminomethylphenylcarbamoyl)benzyl]carbamic Acid t-butyl EsterYield 109.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The compound (1.95 g) obtained in Example 122-1 was dissolved in chloroform (20 ml) and DMF (8 ml) and then added with WSCI hydrochloride (1.50 g) and HOBt (1.08 g), followed by stirring at room temperature for 1 hour. The compound (1.23 g) obtained in Example 19-2 and chloroform (10 ml) were added to the solution, and the whole was stirred at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (2.86 g) as a yellow oily substance.

Workup

  1. stirringthe whole was stirred at room temperature for 15 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-d24347ddf6f0469fa0e3e2e6b15e09c6
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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