Methanol → 2-(4-(Pyridin-2-ylamino)phenoxy)nicotinic acid

HRID 473747Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:25]=[CH:24][C:11]([O:12][C:13]2[N:23]=[CH:22][CH:21]=[CH:20][C:14]=2[C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=1.[OH-].[Li+].CO.O>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[N:23]=[CH:22][CH:21]=[CH:20][C:14]=2[C:15]([OH:17])=[O:16])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 2-(4-(pyridin-2-ylamino)phenoxy)nicotinate (6.23 g, 18.6 mmol) in THF (0.28 M) was added lithium hydroxide (1.33 g, 55.7 mmol). The reaction was stirred for 16 h before adding an addition equivalent of lithium hydroxide and a volume of methanol and water relative to THF to make a 3:2:1 solution of THF:methanol:water. The resulting suspension was heated to 40° C. for 1.5 h. The solid was filtered away from the filtrate to afford the product as a pale orange solid. MS (ESI, pos. ion) m/z: 308.0 (M+1). IC50 (uM) 8.955.

Workup

filtrationThe solid was filtered away from the filtrate

Sources & evidence

ORD record: ord-180fb8c32d04402a87f6d8862c677add
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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