1-Hydroxybenzotriazole → HCID 86625486, compound

HRID 2263014Notes

Reaction equation

HRID 2263014 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][NH:27][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.[C:52]([O:56][C:57]([NH:59][CH2:60][C:61](O)=[O:62])=[O:58])([CH3:55])([CH3:54])[CH3:53]>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][N:27]([C:61](=[O:62])[CH2:60][NH:59][C:57](=[O:58])[O:56][C:52]([CH3:53])([CH3:54])[CH3:55])[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 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68777752HCID 68777752, compound

Product 1

HCID 86625486HCID 86625486, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-1,2-benzisoxazol-3-yl-4-(3-piperazin-1-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide (100 mg, 0.241 mmol), 1-hydroxybenzotriazole (32.5 mg, 0.241 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (92.5 mg, 0.482 mmol) and N-(tert-butoxycarbonyl)glycine (42.3 mg, 0.241 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 102 mg (73.9%) 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-6d1057f6222d4e1f8a7b241e3282f99c
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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