1-Hydroxybenzotriazole → HCID 9804230, compound

HRID 1352662Notes

Reaction equation

HRID 1352662 reaction equation
[Cl:1][C:2]1[C:19]([Cl:20])=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15](O)=[O:16])=[CH:11][CH:10]=3)[NH:8][C:4]=2[CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:43][N:44]1[C:49]([CH3:51])([CH3:50])[CH2:48][CH:47]([NH2:52])[CH2:46][C:45]1([CH3:54])[CH3:53]>C1COCC1>[Cl:1][C:2]1[C:19]([Cl:20])=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[CH:11][C:12]([C:15]([NH:52][CH:47]4[CH2:46][C:45]([CH3:53])([CH3:54])[N:44]([CH3:43])[C:49]([CH3:51])([CH3:50])[CH2:48]4)=[O:16])=[CH:13][CH:14]=3)[NH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 40731194-(5,6-dichloro-1H-benzimidazol-2-yl)benzoic acid

Product 1

HCID 9804230HCID 9804230, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 5,6-dichloro-2-(4-carboxyphenyl)benzimidazole (0.3 g, 0.9 mmol) prepared as described in Preparation 8, 1-hydroxybenzotriazole (0.145 g, 1.08 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.207 g, 1.08 mmol) in THF (10 ml) was heated at 35–40° C. for 1 h. 1,2,2,6,6,-Pentamethyl-4-aminopiperidine in THF (2 ml) was added dropwise and the reaction was refluxed for 1 h. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was treated with 2N NaOH (5 ml). The solid was filtered, washed with water and dried at 50° C. under vacuum. The solid was suspended in isopropyl alcohol and stirred for half an hour, filtered and dried to give 91 mg of the title compound (yield 22%) as an yellow powder, mp>280° C.

Workup

  1. customprepared
  2. temperaturewas heated at 35–40° C. for 1 h
  3. temperaturethe reaction was refluxed for 1 h
  4. customthe solvent was removed under reduced pressure
  5. additionthe residue was treated with 2N NaOH (5 ml)
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried at 50° C. under vacuum
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-175c97a8914a466f9e126cf341ba6d0f
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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