Dichloromethane → 1-[6-(2-Acetylsulfamoylphenyl)pyridin-3-ylmethyl]-5-propyl-1H-pyrazole-3-carboxylic Acid

HRID 1803794Notes

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:20]=[CH:19][C:18]([CH2:21][N:22]2[C:26]([CH2:27][CH2:28][CH3:29])=[CH:25][C:24]([C:30]([OH:32])=[O:31])=[N:23]2)=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])(C)C.C(O)(C(F)(F)F)=[O:34].C(Cl)Cl.C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:20]=[CH:19][C:18]([CH2:21][N:22]2[C:26]([CH2:27][CH2:28][CH3:29])=[CH:25][C:24]([C:30]([OH:32])=[O:31])=[N:23]2)=[CH:17][CH:16]=1)(=[O:8])=[O:7])(=[O:34])[CH3:4]

Participants

Conditions

Temperature: 40 °C

Procedure

1-[6-(2-t-Butylsulfamoylphenyl)pyridin-3-ylmethyl]-5-propyl-1H-pyrazole-3-carboxylic acid (480 mg, 1.0 mmol) was dissolved in TFA (2.8 mL, 36.8 mmol) and heated at 40° C. for 3 hours. The mixture was diluted with toluene and concentrated (azeotrope ×3). The residue was dissolved in DCM (5.53 mL, 86.2 mmol), then triethylamine (1.8 mL, 12.6 mmol) and acetic anhydride (992 μL, 10.5 mmol) were added. The resulting solution was stirred at room temperature for 1 hour. Additional triethylamine and acetic anhydride were added to drive the reaction. The reaction was then quenched with water (150 μL) and dried through azeotrope with toluene to yield the title compound (108 mg), which was used without further purification.

Workup

concentrationconcentrated (azeotrope ×3)
customthe reaction
customThe reaction was then quenched with water (150 μL)
dry with materialdried through azeotrope with toluene

Sources & evidence

ORD record: ord-bf5b25856f314e25ad94b5f775da35f2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08350027B2

Reaction notes

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