Hydrochloric Acid → 6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid pentafluorophenyl ester

HRID 1972055Notes

Reaction equation

[CH2:1]([C:5]1[N:10]=[N:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.FC(F)(F)C(O[C:38]1[C:43]([F:44])=[C:42]([F:45])[C:41]([F:46])=[C:40]([F:47])[C:39]=1[F:48])=O.Cl>C(Cl)Cl>[F:44][C:43]1[C:38]([O:12][C:11]([C:8]2[N:9]=[N:10][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:6]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:18][CH:19]=3)[CH:7]=2)=[O:13])=[C:39]([F:48])[C:40]([F:47])=[C:41]([F:46])[C:42]=1[F:45]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of the carboxylic acid (24.4 mmol, 8.6 g) in DCM (100 mL) was added pyridine (81 mmol, 6.4 g) followed pentafluorophenyl trifluoroacetate (40.52 mmol, 11.3 g) drop-wise. The reaction was stirred at 0° C. for 30 min and then at room temperature for 8 h. The reaction was added to 1N HCl (100 mL), and the product was extracted with ethyl acetate. The crude product was purified using a mixture of hexanes in ethyl acetate on a 330 g silica gel ISCO column to provide 6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid pentafluorophenyl ester (9.0 g).

Workup

waitat room temperature for 8 h
extractionthe product was extracted with ethyl acetate
customThe crude product was purified
additiona mixture of hexanes in ethyl acetate on a 330 g silica gel ISCO column

Sources & evidence

ORD record: ord-606b9f5014984eee81759e2c2f8201e2
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431575B2

Reaction notes

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