Hydrochloric Acid → HCID 11223561, compound

HRID 2109943Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([NH:13][C:14]2[N:24]=[CH:23][CH:22]=[CH:21][C:15]=2[C:16]([O:18]CC)=[O:17])=[CH:11][C:10]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[N:9]1.O.[OH-].[Li+].Cl>C(O)C.C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([NH:13][C:14]2[N:24]=[CH:23][CH:22]=[CH:21][C:15]=2[C:16]([OH:18])=[O:17])=[CH:11][C:10]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[N:9]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 2-{[1-(2-chlorophenyl)-3-(4-fluorophenyl)-1H-pyrazol-5-yl]amino}nicotinate (410 mg, 0.94 mmol) in a mixture of ethanol (4 mL) and THF (4 mL) was added lithium hydroxide monohydrate (115 mg, 2.74 mmol) in water (8 mL), and the mixture was then heated to 40° C. for 1 h. The reaction mixture was cooled to rt, and the pH of the solution was adjusted to 5 by addition of 0.5 N hydrochloric acid solution (the mixture turned cloudy). The solid was filtered off and washed with more water. The solid was dried in a vacuum oven at 60° C. to give 380 mg of the desired product (99%). 1H NMR (300 MHz, CD2Cl2) δ 10.18 (s, 1H), 8.45 (dd, 1H), 8.24 (dd, 1H), 7.87 (dd, 2H), 7.47-7.62 (m, 4H), 7.23 (s, 1H), 7.12 (t, 2H), 6.85 (dd, 1H); ES-MS m/z 351.2 (MH+); HPLC RT (min) 2.58.

Workup

temperatureThe reaction mixture was cooled to rt
filtrationThe solid was filtered off
washwashed with more water
customThe solid was dried in a vacuum oven at 60° C.

Sources & evidence

ORD record: ord-1652101524254bb18a4b76a756b45861
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517878B2

Reaction notes

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