Hydrochloric Acid → (RS)-S-[4-({5-bromo-4-[(1R,2R)-2-hydroxy-1-methylpropoxy]pyrimidin-2-yl}amino)phenyl]-N-(ethoxycarbonyl)-S-ethyl Sulfoximide

HRID 1391445Notes

Reaction equation

HRID 1391445 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:16][CH3:17])(=[N:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[CH:4][CH:3]=1.[Br:18][C:19]1[C:20]([O:26][C@H:27]([CH3:31])[C@H:28]([OH:30])[CH3:29])=[N:21][C:22](Cl)=[N:23][CH:24]=1.Cl>C(#N)C.O1CCOCC1>[Br:18][C:19]1[C:20]([O:26][C@H:27]([CH3:31])[C@H:28]([OH:30])[CH3:29])=[N:21][C:22]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH2:16][CH3:17])(=[N:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[CH:4][CH:3]=2)=[N:23][CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 59673998Benzenamine, 4-[N-(Ethoxycarbonyl)-S-Ethylsulfonimidoyl]HCID 59674033(2R,3R)-3-(5-bromo-2-chloropyrimidin-4-yloxy)butan-2-ol

Product 1

HCID 59674022(RS)-S-[4-({5-bromo-4-[(1R,2R)-2-hydroxy-1-methylpropoxy]pyrimidin-2-yl}amino)phenyl]-N-(ethoxycarbonyl)-S-ethyl Sulfoximide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

128 mg (0.51 mmol) of (RS)-S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-ethyl sulfoximide and 150 mg (0.53 mmol) of (2R,3R)-3-[(5-bromo-2-chloropyrimidin-4-yl)oxy]-butan-2-ol in 2 ml of acetonitrile are mixed with 0.12 ml of a 4N solution of HCl in dioxane. The batch is stirred for 2 days at 60° C. The solvent is removed, and the residue is purified by chromatography (DCM/EtOH 95:5). 43 mg (0.09 mmol, corresponding to 17% of theory) of the product is obtained.

Workup

  1. customThe solvent is removed
  2. customthe residue is purified by chromatography (DCM/EtOH 95:5)
  3. custom43 mg (0.09 mmol, corresponding to 17% of theory) of the product is obtained

Sources & evidence

ORD record
ord-765c896ddca2486fa786c611f5aa0ff4
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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