Sodium Hydroxide → HCID 86760590, compound

HRID 970436Notes

Reaction equation

HRID 970436 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH:10]([CH2:32][OH:33])[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]([N:27]=[CH:28][N:29]([CH3:31])[CH3:30])(=[O:26])=[O:25])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[OH-].[Na+]>C1COCC1.Cl.C(OCC)(=O)C>[NH2:21][C:19]1[CH:18]=[CH:17][C:16]([S:24]([N:27]=[CH:28][N:29]([CH3:30])[CH3:31])(=[O:26])=[O:25])=[C:15]([O:14][CH2:13][CH2:12][CH2:11][C@H:10]([NH:9][C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=2)[CH2:32][OH:33])[CH:20]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 72491588HCID 72491588, compound

Product 1

HCID 86760590HCID 86760590, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 145 mg (0.30 mmol) of 2-[4-(5-bromo-2-chloro-pyrimidin-4-ylamino)-5-hydroxy-pentyloxy]-N-dimethylaminomethylene-4-nitro-benzenesulfonamide in 20 ml of THF is mixed under argon at room temperature with 2.0 ml of an approximately 10% solution of Ti(III)Cl in 20-30% hydrochloric acid. After 2 hours, the reaction solution is mixed again with 0.3 ml of Ti(III)Cl solution, and it is stirred for another 18 hours. The batch is diluted with ethyl acetate and made basic with 1N NaOH solution. The phases are separated, and the aqueous phase is extracted again from ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (DCM/methanol 9:1; Flashmaster II). 90 mg (0.17 mmol, corresponding to 56% of theory) of the product is obtained.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted again from ethyl acetate
  3. dry with materialThe combined organic phases are dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe remaining residue is purified by chromatography (DCM/methanol 9:1; Flashmaster II)
  7. custom90 mg (0.17 mmol, corresponding to 56% of theory) of the product is obtained

Sources & evidence

ORD record
ord-f5eff830c59f4695bdd51754d404f717
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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