1-Hydroxybenzotriazole → HCID 23155398, compound

HRID 2080845Notes

Reaction equation

HRID 2080845 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].CCN=C=NCCCN(C)C.Cl.C1C=CC2N([OH:32])N=NC=2C=1.N1C=CN=C1CN(C[C:47]1[CH:70]=[CH:69][C:50]([CH2:51][N:52]([CH2:58][CH2:59][CH2:60][CH2:61]N(CCC)CCC)[CH2:53]CC(O)=O)=CC=1)CC1NC=CN=1>CN(C=O)C>[NH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[NH:1][C:47](=[O:32])[CH2:70][CH2:69][CH2:50][CH2:51][N:52]1[CH2:53][CH2:61][CH2:60][CH2:59][CH2:58]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 7372853,4-DiaminobenzonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11950441HCID 11950441, compound

Product 1

HCID 23155398HCID 23155398, compoundYield 214.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Commercially available 3,4-diaminobenzonitrile (0.461 g) was dissolved in DMF (18.4 ml) and added with WSCI hydrochloride (0.996 g), HOBt (0.702 g), and the compound (0.844 g) obtained in Example 60-1 and the whole was stirred at room temperature for 3 days. The reaction solution was concentrated under reduced pressure. The residue was added with water and subjected to separation/extraction with chloroform. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (1.04 g) as a yellow oily substance.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe residue was added with water
  3. extractionsubjected to separation/extraction with chloroform
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-e09ea3de60494fee8b80558f5644b368
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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