Hydrochloric Acid → HCID 58012040, compound

HRID 660953Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17]([O:19]C)=[O:18])[C:11](=[O:24])[N:10]([CH2:25][C:26]([NH:28][C:29]([CH3:41])([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[CH3:30])=[O:27])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>CO.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17]([OH:19])=[O:18])[C:11](=[O:24])[N:10]([CH2:25][C:26]([NH:28][C:29]([CH3:41])([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[CH:32]=3)[CH3:30])=[O:27])[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

180 mg (0.31 mmol) of methyl 3-(3-(4-chlorophenyl)-1-[2-(1-methyl-1-[3-(trifluoromethyl)phenyl]-ethylamino)-2-oxoethyl]-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-ylmethyl)-benzoate (Example 411) are dissolved in 3 ml of methanol and 3 ml of THF, treated with 0.3 ml of 2 N aqueous sodium hydroxide and stirred for 1 hr at 70° C. The reaction mixture is then introduced into ca. of 10 ml water, brought to pH 4 with 1 N hydrochloric acid, and stirred for 2 hrs at RT. The resulting precipitate is filtered off at the pump, washed with water and freed of solvent residues under high vacuum. 154 mg (88% of theory) of the target compound are obtained.

Workup

stirringstirred for 2 hrs at RT
filtrationThe resulting precipitate is filtered off at the pump
washwashed with water
custom154 mg (88% of theory) of the target compound are obtained

Sources & evidence

ORD record: ord-ff81154cb9a3409a8955d03e555df8c9
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084481B2

Reaction notes

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