Hydrochloric Acid → HCID 44139914, compound

HRID 1913194Notes

Reaction equation

HRID 1913194 reaction equation
[ClH:1].[O:2]=[C:3]1[N:7]([C:8]2[N:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)[NH:6][CH:5]=[C:4]1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.Cl.O>C(O)(=O)C.O1CCOCC1.[Pd]>[ClH:1].[ClH:1].[NH2:15][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([N:7]2[C:3](=[O:2])[C:4]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[CH:5][NH:6]2)=[N:13][CH:12]=1

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 68716599HCID 68716599, compound

Product 1

HCID 44139914HCID 44139914, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

10.0 g (38.0 mmol) of the compound from Example 12 are initially charged in 300 ml of acetic acid. 20 ml of a 4 N solution of hydrogen chloride in dioxane and 5.0 g (4.7 mmol) of palladium on carbon (10%) are added and the mixture is hydrogenated at RT under atmospheric pressure for 96 h. Water is then added until the organic solid formed has gone back into solution, and the catalyst is filtered off through silica gel. The filtrate is concentrated and the residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate mixture). The product obtained is then stirred in a 4 N solution of hydrogen chloride in dioxane for 30 min, and the solid is filtered off and dried under high vacuum. The solid is then dissolved in about 300 ml of water, and the solution is lyophilized.

Workup

  1. customformed
  2. filtrationthe catalyst is filtered off through silica gel
  3. concentrationThe filtrate is concentrated
  4. customthe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate mixture)
  5. customThe product obtained
  6. filtrationthe solid is filtered off
  7. customdried under high vacuum
  8. dissolutionThe solid is then dissolved in about 300 ml of water

Sources & evidence

ORD record
ord-eca1a1287b4445ba8282aaec838411c9
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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