1-Hydroxybenzotriazole → HCID 66941341, compound

HRID 1173876Notes

Reaction equation

HRID 1173876 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2].[NH:23]1[CH:27]=[CH:26][N:25]=[C:24]1[CH2:28][N:29]([CH2:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1)[CH2:30][C:31]1[NH:32][CH:33]=[CH:34][N:35]=1.C1C=CC2N(O)N=NC=2C=1.N=C=N>CN(C=O)C>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:41](=[O:42])[C:40]2[CH:44]=[CH:45][C:37]([CH2:36][N:29]([CH2:28][C:24]3[NH:23][CH:27]=[CH:26][N:25]=3)[CH2:30][C:31]3[NH:32][CH:33]=[CH:34][N:35]=3)=[CH:38][CH:39]=2)=[CH:19][CH:20]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 160435Carbodiimide2×HCID 66941790HCID 66941790, compoundHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Product 1

HCID 66941341HCID 66941341, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (150 mg) obtained in Example 34-3 was dissolved in DMF (3.0 ml) and then added with the compound (140 mg) synthesized in Example 2-2. To the mixture solution, HOBt (79.0 mg) and PS-carbodiimide (manufactured by Argonaut Technologies, Inc.) (681 mg) were added, followed by stirring at room temperature for 18 hours. After completion of the reaction, PS-carbodiimide was filtrated and DMF in the filtrate was then distilled off. The residue was added with chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution and saturated saline solution. The residue was brought into an anhydrous state using anhydrous sodium sulfate and then concentrated. Subsequently, the concentrated product was purified through column chromatography (chloroform/methanol), thereby obtaining the subject compound (105 mg) as a white solid.

Workup

  1. filtrationwas filtrated
  2. distillationDMF in the filtrate was then distilled off
  3. additionThe residue was added with chloroform
  4. washwashed with a 1 mol/l sodium hydroxide aqueous solution and saturated saline solution
  5. concentrationconcentrated
  6. customSubsequently, the concentrated product was purified through column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-f9c6f3d1cf524bb7a05e39dfdd1f4547
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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