1-Hydroxybenzotriazole → HCID 58801892, compound

HRID 348699Notes

Reaction equation

HRID 348699 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH:46]1([N:52]([CH3:58])[CH2:53][CH2:54][CH2:55][CH2:56][NH2:57])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C=O)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:57][CH2:56][CH2:55][CH2:54][CH2:53][N:52]([CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)[CH3:58])=[O:21])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7138422HCID 7138422, compoundHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Product 1

HCID 58801892HCID 58801892, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The compound (120 mg) obtained in Example 2-2 was dissolved in anhydrous DMF (3.0 ml) and added with WSCI hydrochloride (103.3 mg) and HOBt (72.8 mg). Then, the solution was added with a solution of the compound (76.0 mg) obtained in Example 98-2 in DMF and stirred for 18 hours. After the reaction, the solvent was distilled off and the residue was then added with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The extract was washed with saturated saline solution and dried with magnesium sulfate, followed by distilling the solvent off. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (20.4 mg) of the subject compound as a white solid.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionthe residue was then added with a 1 mol/l sodium hydroxide aqueous solution
  4. extractionfollowed by extraction with chloroform
  5. washThe extract was washed with saturated saline solution
  6. dry with materialdried with magnesium sulfate
  7. distillationby distilling the solvent off
  8. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/methanol)
  9. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-0495bbbfd5564092a9250f988239aef0
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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