Lithium Hydroxide → 6'-{[(Ethylamino)carbonyl]amino}-5''-fluoro-3,3':4',3''-terpyridine-5-carboxylic acid

HRID 2243034Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[CH:18]=2)=[C:9]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([F:30])[CH:29]=2)[CH:8]=1)=[O:5])[CH3:2].[OH-].[Li+]>C1COCC1>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[CH:18]=2)=[C:9]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([F:30])[CH:29]=2)[CH:8]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

Ethyl 6′-{[(ethylamino)carbonyl]amino}-5″-fluoro-3,3′:4′,3″-terpyridine-5-carboxylate (Example 68, 0.19 g, 0.46 mmol) was added to a 25 mL round-bottomed flask with THF (3 mL) to give a white suspension. Lithium hydroxide (1.160 mL, 1.16 mmol) was added to the mixture, and the solution was stirred at 45° C. for 2 h. The solvent was removed under reduced pressure, and the resulting residue was diluted with water and adjusted to pH˜4 by 2N HCl. The precipitate that formed was collected by filtration, washed with water, and dried to give the title compound as a white solid (154 mg). MS (ESP): 382 (MH+) for C19H16FN5O3; NMR: 1.08 (t, 3H), 3.13-3.24 (m, 2H), 7.63 (s, 1H) 7.64-7.68 (m, 1H) 7.69-7.77 (m, 1H), 7.93 (t, 1H), 8.19 (t, 1H), 8.36 (s, 1H), 8.45 (d, 1H), 8.55 (d, 1H), 8.90 (d, 1H), 9.45 (s, 1H).

Workup

customto give a white suspension
customThe solvent was removed under reduced pressure
additionthe resulting residue was diluted with water
customThe precipitate that formed
filtrationwas collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-ae79a97238614c648c1ffc2201cb603d
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

Loading…