Hydrochloric Acid → HCID 58032630, compound

HRID 1046843Notes

Reaction equation

O.[C:2](=[O:5])([O-:4])[O-].[K+].[K+].[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[N:21]3[N:22]=[C:23]([N:25]4C(=O)[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[C:26]4=[O:35])[N:24]=[C:20]3[N:19]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=3)[C:18]([CH3:46])=[C:17]2[C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:12][CH:11]=1)#[N:9].Cl>C(O)C>[C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[N:21]3[N:22]=[C:23]([NH:25][C:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=4[C:2]([OH:4])=[O:5])=[O:35])[N:24]=[C:20]3[N:19]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:43])([F:45])[F:44])[CH:37]=3)[C:18]([CH3:46])=[C:17]2[C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:14][CH:15]=1)#[N:9]

Participants

Conditions

Temperature: 50 °C

Procedure

Water (1 ml) and potassium carbonate (23.1 mg, 167 μmol, 2 eq.) were added to a solution of ethyl 7-(4-cyanophenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-methyl-4-[3-(trifluoromethyl)-phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate (50.0 mg, 83.5 μmol; Example 1) in ethanol (6.25 ml). In a closed, pressure-proof glass tube, the reaction mixture was heated at 50° C. 1 N hydrochloric acid (670 μl, 670 μmol, 8 eq.) was then added, the reaction mixture was concentrated under reduced pressure and the residue was purified by preparative HPLC (Gromsil C18 column, 10 μm, 250×30 mm; mobile phase: acetonitrile-water-0.1% TFA 10:90→100:0). This gave the product as a solid (45 mg, 87% of theory).

Workup

concentrationthe reaction mixture was concentrated under reduced pressure
customthe residue was purified by preparative HPLC (Gromsil C18 column, 10 μm, 250×30 mm; mobile phase: acetonitrile-water-0.1% TFA 10:90→100:0)

Sources & evidence

ORD record: ord-335c6af5617742e6a6501f93c9993904
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569314B2

Reaction notes

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