Sodium Hydroxide → HCID 17986356, compound

HRID 970431Notes

Reaction equation

HRID 970431 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:16]=2[S:24]([NH2:27])(=[O:26])=[O:25])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[OH-].[Na+]>C1COCC1.Cl>[NH2:21][C:19]1[CH:18]=[CH:17][C:16]([S:24]([NH2:27])(=[O:26])=[O:25])=[C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=2)[CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 17986371HCID 17986371, compound

Product 1

HCID 17986356HCID 17986356, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 160 mg (0.33 mmol) of 2-[4-(5-bromo-2-chloro-pyrimidin-4-ylamino)-butoxy]-4-nitro-benzenesulfonamide in 10 ml of THF is mixed under argon at room temperature with 1.4 ml of a 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid. After 4 hours, the reaction solution is again mixed with 0.2 ml of the Ti(III)Cl solution and stirred for another 14 hours. The batch is made basic with 2N NaOH solution and then filtered. The filter cake is rewashed 2× with 50 ml of ethyl acetate/MeOH (30 ml/20 ml) in each case. 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 (MgSO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (dichloromethane/methanol 9:1; Flashmaster II). 70 mg (0.81 mmol, corresponding to 47% 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 (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customThe remaining residue is purified by chromatography (dichloromethane/methanol 9:1; Flashmaster II)
  9. custom70 mg (0.81 mmol, corresponding to 47% of theory) of the product is obtained

Sources & evidence

ORD record
ord-a3ab82c7d05a4a0a9c9486fc846d0a11
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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