Sodium Chloride → HCID 58985726, compound

HRID 1169796Notes

Reaction equation

HRID 1169796 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[N:15]=[N:16][N:17]([CH3:19])[N:18]=3)=[CH:12][N:11]=[C:10]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:35])(=[N:29]C(OCC)=O)=[O:28])=[CH:23][CH:22]=3)[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])C.[Na+].[Na+].[Cl-]>C(O)C>[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[N:15]=[N:16][N:17]([CH3:19])[N:18]=3)=[CH:12][N:11]=[C:10]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([S:27]([CH3:35])(=[NH:29])=[O:28])=[CH:25][CH:26]=3)[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 2723922Sodium ethoxide2×HCID 58985539HCID 58985539, compound

Product 1

HCID 58985726HCID 58985726, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

117 mg (0.23 mmol) (RS)—S-(4-{[4-(cyclohexylamino)-5-(2-methyl-2H-tetrazol-5-yl)pyrimidine-2-yl]amino}phenyl)-N-(ethoxycarbonyl)-S-methylsulfoximide) (Ex. 3.1) in 1.7 ml ethanol are treated with 0.4 mL (0.61 mmol) of a freshly prepared 1.53 molar sodium ethanolate solution and stirred for 7 hours at 60° C. The mixture is diluted with 2 mL ethanol and then treated with a further 1.0 ml (1.53 mmol) of the 1.53 molar sodium ethanolate solution. After 24 hours at 60° C., the mixture is heated to 70° C. and stirred for a further 20 hours. The mixture is treated with saturated NaCl solution and extracted with THF. The combined organic phases are dried (Na2SO4), filtered and concentrated. The resulting residue is chromatographically (DCM/EtOH 95:5) purified. 76 mg (0.18 mmol, corresponding to 76% of theor.) of the product is obtained.

Workup

  1. waitAfter 24 hours at 60° C.
  2. temperaturethe mixture is heated to 70° C.
  3. stirringstirred for a further 20 hours
  4. extractionextracted with THF
  5. dry with materialThe combined organic phases are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified
  9. custom76 mg (0.18 mmol, corresponding to 76% of theor.) of the product is obtained

Sources & evidence

ORD record
ord-241149ebb35a4a3fa0ad3b071c6a14a1
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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