Sodium Hydroxide → HCID 59020384, compound

HRID 970417Notes

Reaction equation

HRID 970417 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH:11]([OH:26])[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+]>O1CCCC1.Cl>[NH2:23][C:19]1[CH:18]=[C:17]([S:14]([NH:13][CH2:12][CH:11]([OH:26])[CH2:10][NH: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 17986384HCID 17986384, compound

Product 1

HCID 59020384HCID 59020384, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 258 mg (0.553 mmol) of N-[3-(5-bromo-2-chloro-pyrimidin-4-ylamino)-2-hydroxy-propyl]-3-nitro-benzenesulfonamide in 20 ml of tetrahydrofuran is mixed under argon at room temperature with 2.6 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 60 minutes. The batch is made basic with 1 M 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 (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (dichloromethane/MeOH 95:5, Flashmaster II). 155 mg (0.36 mmol, corresponding to 64% 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 (dichloromethane/MeOH 95:5, Flashmaster II)
  9. custom155 mg (0.36 mmol, corresponding to 64% of theory) of the product is obtained

Sources & evidence

ORD record
ord-a2cc97004a404894861180c930db7b54
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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