1-Hydroxybenzotriazole → HCID 68778578, compound

HRID 2263011Notes

Reaction equation

HRID 2263011 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]([OH:32])=O)[CH2:26][CH2:25]4)[N:20]=3)[CH2:15][CH2:14]2)=[O:12])=[N:2]1.O[N:34]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.O.N>CN(C)C=O.O>[NH2:34][C:30]([CH:27]1[CH2:26][CH2:25][N:24]([C:21]2[N:20]=[C:19]([N:16]3[CH2:17][CH2:18][N:13]([C:11]([NH:10][C:3]4[C:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=5[O:1][N:2]=4)=[O:12])[CH2:14][CH2:15]3)[S:23][N:22]=2)[CH2:29][CH2:28]1)=[O:32]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12896473Azane;hydrateHCID 68777919HCID 68777919, compound

Product 1

HCID 68778578HCID 68778578, compoundYield 74.9%

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 (70.0 mg, 0.153 mmol), 1-hydroxybenzotriazole (23.4 mg, 0.153 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (44.1 mg, 0.230 mmol) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 1 hour. 25% Ammonia water (33.8 mg, 0.497 mmol) was added thereto under ice-cooling, and the resulting mixture was stirred at room temperature for 0.5 hour. 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 52.3 mg (74.9%) of the desired product as a solid.

Workup

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

Sources & evidence

ORD record
ord-20c32d750fb5475fb600d2483df6657e
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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