1-Hydroxybenzotriazole → HCID 86625485, compound

HRID 2263012Notes

Reaction equation

HRID 2263012 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[S:23][N:22]=[C:21]([N:24]4[CH2:29][CH2:28][CH:27]([C:30](O)=[O:31])[CH2:26][CH2:25]4)[N:20]=3)[CH2:15][CH2:14]2)=[O:12])=[N:2]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:55][CH2:56][CH2:57][NH:58][C:59](=[O:65])[O:60][C:61]([CH3:64])([CH3:63])[CH3:62]>CN(C)C=O.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][C:11]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[S:23][N:22]=[C:21]([N:24]4[CH2:25][CH2:26][CH:27]([C:30]([NH:55][CH2:56][CH2:57][NH:58][C:59](=[O:65])[O:60][C:61]([CH3:63])([CH3:62])[CH3:64])=[O:31])[CH2:28][CH2:29]4)[N:20]=3)[CH2:17][CH2:18]2)=[O:12])=[N:2]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68777919HCID 68777919, compound

Product 1

HCID 86625485HCID 86625485, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(5-{4-[(1,2-benzisoxazol-3-ylamino)carbonyl]piperazin-1-yl}-1,2,4-thiadiazol-3-yl)piperidine-4-carboxylic acid (100 mg, 0.219 mmol), 1-hydroxybenzotriazole (29.6 mg, 0.219 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (84.0 mg, 0.438 mmol) and tert-butyl N-(2-aminoethyl)carbamate (35.0 mg, 0.219 mmol) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 12 hours. The reaction mixture was poured to water, and a solid was separated by filtration, which was recrystallized from a mixed solvent of tetrahydrofuran, ethyl acetate and hexane to give 111 mg (84.7%) of the desired product as a solid.

Workup

  1. customa solid was separated by filtration, which
  2. customwas recrystallized from a mixed solvent of tetrahydrofuran, ethyl acetate and hexane

Sources & evidence

ORD record
ord-9f4d50784d414e6ca9198e1e103ee2ae
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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