N'-Hydroxy-4-(trifluoromethyl)benzene-1-carboximidamide → HCID 86684874, compound

HRID 238375Notes

Reaction equation

HRID 238375 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)[NH2:4].[CH3:15][N:16]1[C:20]([C:21](O)=O)=[CH:19][CH:18]=[N:17]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.CC(C)([O-])C.[K+]>O.O1CCCC1>[CH3:15][N:16]1[C:20]([C:21]2[O:1][N:2]=[C:3]([C:5]3[CH:6]=[CH:7][C:8]([C:11]([F:13])([F:12])[F:14])=[CH:9][CH:10]=3)[N:4]=2)=[CH:19][CH:18]=[N:17]1

Participants

8

Reactant 5

HCID 609329N'-Hydroxy-4-(trifluoromethyl)benzene-1-carboximidamideHCID 6431581-methyl-1H-pyrazole-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86684874HCID 86684874, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

N′-hydroxy-4-(trifluoromethyl)benzene carboximidamide (450 mg) was added to a tetrahydrofuran (8.8 mL) suspension that contained 1-methyl-1H-pyrazol-5-carboxylic acid (450 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (465 mg) and 1-hydroxybenzotriazole monohydrate (328 mg) at a room temperature, and the obtained solution was then stirred for 16 hours. Thereafter, potassium tert-butoxide (1.11 g) and tetrahydrofuran (4.4 mL) were added to the reaction solution, and the obtained mixture was then stirred at a room temperature for 3 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=75:25 to 50:50), so as to obtain the title compound (193 mg) in the form of a colorless solid.

Workup

  1. customat a room temperature
  2. stirringthe obtained mixture was then stirred at a room temperature for 3 hours
  3. extractionthe obtained mixture was then extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated saline
  5. dry with materialwas then dried over anhydrous magnesium sulfate
  6. concentrationfollowed by vacuum concentration
  7. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=75:25 to 50:50)

Sources & evidence

ORD record
ord-ce571f2915bd4303891d1f4cd029e9f4
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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