Sodium Chloride → HCID 58985703, compound

HRID 1169797Notes

Reaction equation

HRID 1169797 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[N:18]([CH3:19])[N:17]=[N:16][N:15]=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:18]([CH3:19])[N:17]=[N:16][N:15]=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 ethoxideHCID 58985664HCID 58985664, compound

Product 1

HCID 58985703HCID 58985703, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

12 mg (0.024 mmol) (RS)—S-(4-{[4-(cyclohexylamino)-5-(1-methyl-1H-tetrazol-5-yl)pyrimidine-2-yl]amino}phenyl)-N-(ethoxycarbonyl)-S-methylsulfoximide (Ex. 3.2) in 1.2 ml ethanol are treated with 0.12 mL (0.18 mmol) of a freshly prepared 1.53 molar sodium ethanolate solution and stirred for 18 hrs at 70° C. 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 digested with MTB ether. 9 mg (0.021 mmol, corresponding to 86% of theor.) of the product is obtained.

Workup

  1. extractionextracted with THF
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custom9 mg (0.021 mmol, corresponding to 86% of theor.) of the product is obtained

Sources & evidence

ORD record
ord-f0b94ae7d9844f9dabfcb171c5467f50
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

Loading…