Hydrochloric Acid → HCID 66628373, compound

HRID 1046844Notes

Reaction equation

HRID 1046844 reaction equation
O.[C:2](=[O:5])([O-])[O-:3].[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]#[N:48])=[CH:12][CH:11]=1)#[N:9].Cl>C(O)C>[C:47]([C:17]1[CH:16]([C:13]2[CH:14]=[CH:15][C:10]([C:8]#[N:9])=[CH:11][CH:12]=2)[N:21]2[N:22]=[C:23]([NH:25][C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:2]([OH:3])=[O:5])=[O:35])[N:24]=[C:20]2[N:19]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:44])([F:43])[F:45])[CH:37]=2)[C:18]=1[CH3:46])#[N:48]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium Carbonate2×HCID 46841071HCID 46841071, compound

Product 1

HCID 66628373HCID 66628373, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

Water (0.5 ml) and potassium carbonate (8.1 mg, 59 mmol) were added to a solution of 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-carbonitrile (25.0 mg, 45.3 μmol; Example 3) in ethanol (3.4 ml). In a closed pressure-proof glass tube, the reaction mixture was heated at 55° C. For complete conversion, more potassium carbonate was added in two separate portions (5 mg, 36 mmol in total), and the mixture was once more heated at 55° C. 1 N hydrochloric acid (180 μl, 180 mmol) was then added, the reaction mixture was concentrated under reduced pressure and the residue was purified by preparative HPLC (Kromasil C18 column, 250×30 mm; mobile phase: acetonitrile-water-0.1% TFA 10:90→100:0). This gave the product as a solid (24.8 mg, 96% of theory).

Workup

  1. customseparate portions (5 mg, 36 mmol in total)
  2. temperaturethe mixture was once more heated at 55° C
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by preparative HPLC (Kromasil C18 column, 250×30 mm; mobile phase: acetonitrile-water-0.1% TFA 10:90→100:0)

Sources & evidence

ORD record
ord-ef2fd668f2fb4be49313d211c28b7b46
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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