Water → HCID 86751876, compound

HRID 725755Notes

Reaction equation

[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=O)[N:9]=2)=[CH:5][C:4]([CH3:17])=[N:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34].O>O1CCCC1>[F:30][C:31]1[CH:32]=[C:33]([NH:34][C:14]([C:10]2[N:9]=[C:8]([O:7][C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:17])[CH:5]=3)[CH:13]=[CH:12][CH:11]=2)=[O:16])[CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-(1',3'-dimethyl-pyrazol-5-yloxy)-pyridine-6-carboxylic acid (2.2 g, 9.6 mmol) (from Example 53) in anhydrous tetrahydrofuran (20 ml) was added carbonyldiimidazole (1.6 g, 10.6 mmol) and stirred for 30 minutes, maintaining the temperature up to 40° C. 3-fluoroaniline (1.1 ml, 10.6 mmol) was added and the reaction mixture heated to 50° C. After 2 hours, the clear mixture was poured into water (100 ml) and extracted three times with ethyl acetate (50 ml each). The combined extracts were dried with anhydrous magnesium sulphate and the solvent was removed in vacuo. The crude product was purified by flash silica gel column chromatography using hexane/ethyl acetate 1/1. The title compound was obtained as a white solid (1.7 g, 54%), mp 110° C.

Workup

temperaturethe reaction mixture heated to 50° C
waitAfter 2 hours
extractionextracted three times with ethyl acetate (50 ml each)
dry with materialThe combined extracts were dried with anhydrous magnesium sulphate
customthe solvent was removed in vacuo
customThe crude product was purified by flash silica gel column chromatography

Sources & evidence

ORD record: ord-e245ab991044403eaf2b39650d023cdd
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05707932

Reaction notes

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