HCID 66705985, compound → HCID 58073680, compound

HRID 1916193Notes

Reaction equation

HRID 1916193 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]#[C:21][C:22]3[CH:23]=[N:24][C:25]([NH2:28])=[CH:26][CH:27]=3)=[C:18]([CH3:29])[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl>[NH2:28][C:25]1[N:24]=[CH:23][C:22]([C:21]#[C:20][C:19]2[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:15][CH:16]=[N:17][C:18]=2[CH3:29])=[CH:27][CH:26]=1

Participants

3

Reactant 1

HCID 66705985HCID 66705985, compound

Product 1

HCID 58073680HCID 58073680, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 7.5 g (19.1 mmol) 4-[5-(6-Amino-pyridin-3-ylethynyl)-6-methyl-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester in 50 mL 4 M HCl (in dioxane) ist to stirred for 3 hours at room temperature. The reaction mixture is evaporated and the residue is taken up in 50 ml DCM and washed with saturated aqueous NaHCO3 solution. After phase separation the organic solvent is removed under reduced pressure. The residue is taken up in methanol dried over Na2SO4. After 15 hours the suspension is filtered off, the residue is washed with methanol and the solvent is removed under reduced pressure. After drying 5.6 g (100%) of crude product are obtained, which are used without further purification in the next step.

Workup

  1. customThe reaction mixture is evaporated
  2. washwashed with saturated aqueous NaHCO3 solution
  3. customAfter phase separation the organic solvent
  4. customis removed under reduced pressure
  5. dry with materialdried over Na2SO4
  6. filtrationAfter 15 hours the suspension is filtered off
  7. washthe residue is washed with methanol
  8. customthe solvent is removed under reduced pressure
  9. dry with materialAfter drying 5.6 g (100%) of crude product
  10. customare obtained
  11. customwhich are used without further purification in the next step

Sources & evidence

ORD record
ord-bd320218b4724ddfb3897f63ffcba2e7
Source dataset
uspto-grants-2013_12
Patent number
US08618111B2

Reaction notes

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