1-Hydroxybenzotriazole → HCID 86655378, compound

HRID 2190425Notes

Reaction equation

HRID 2190425 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=3)[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[O:16])[CH:8]=[CH:7][C:5]=2[N:6]=1.[O:31]1[CH:35]=[C:34]([C:36](O)=[O:37])[N:33]=[CH:32]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C)C=O.O>[F:26][C:24]([F:27])([F:25])[C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:15]([C:14]2[CH:13]=[C:12]([CH:30]=[CH:29][CH:28]=2)[O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:36]([C:34]4[N:33]=[CH:32][O:31][CH:35]=4)=[O:37])[S:3][C:4]=3[CH:10]=2)=[O:16])=[CH:23][CH:22]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 142814301,3-Oxazole-4-carboxylic acidHCID 86655374HCID 86655374, compound

Product 1

HCID 86655378HCID 86655378, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-N-[4-(trifluoromethyl)phenyl]benzamide (215 mg, 0.50 mmol) produced in Example A25(v), 1,3-oxazole-4-carboxylic acid (113 mg, 1.00 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (192 mg, 1.00 mmol), 1-hydroxybenzotriazole (135 mg, 1.00 mmol) and N-ethyl-N-isopropylpropane-2-amine (260 mg, 2.0 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 18 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1), and triturated with diethyl ether to give the title compound (90 mg, 34%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1)
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-1a30f153f3ee4904afefa2f362199060
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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