Sodium Hydroxide → HCID 59020336, compound

HRID 970423Notes

Reaction equation

HRID 970423 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH2:10][CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=2)(=[O:16])=[O:15])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[OH-].[Na+]>C1COCC1.Cl>[NH2:23][C:19]1[CH:18]=[C:17]([S:14]([NH:13][CH2:12][CH2:11][CH2:10][O:9][C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=2)(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 17986362HCID 17986362, compound

Product 1

HCID 59020336HCID 59020336, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 70 mg (0.16 mmol) of N-[3-(5-bromo-2-chloro-pyrimidin-4-yloxy)-propyl]-3-nitro-benzenesulfonamide in 5 ml of THF is mixed at 0° C. with 1.0 ml of a 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid. After 2 hours, the reaction solution is mixed again with 0.2 ml of Ti(III)Cl solution and stirred for another hour. The batch is made basic with 1N NaOH solution and then filtered. The filter cake is rewashed 2× in each case with 50 ml of ethyl acetate/MeOH (30 ml/20 ml). The filtrate is concentrated by evaporation in a rotary evaporator and then extracted with ethyl acetate (2×). The combined organic phases are washed with NaCl solution, dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate 1:1, Flashmaster II). 32 mg (0.08 mmol, corresponding to 49% of theory) of the product is obtained.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated by evaporation in a rotary evaporator
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic phases are washed with NaCl solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customThe remaining residue is purified by chromatography (hexane/ethyl acetate 1:1, Flashmaster II)
  9. custom32 mg (0.08 mmol, corresponding to 49% of theory) of the product is obtained

Sources & evidence

ORD record
ord-18a468fc7b0b4cdc9ac6d4aff4fff92d
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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