Sodium Hydroxide → HCID 17986363, compound

HRID 970438Notes

Reaction equation

HRID 970438 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-])=O)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[OH-].[Na+]>C1COCC1.Cl.C(OCC)(=O)C>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH2:12][CH2:11][CH2:10][NH:9][C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 17986374HCID 17986374, compound

Product 1

HCID 17986363HCID 17986363, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 500 mg (1.29 mmol) of (5-bromo-2-chloro-pyrimidin-4-yl)-[3-(2-nitro-phenoxy)-propyl]-amine in 20 ml of THF is mixed at room temperature with 6.0 ml of an approximately 10% solution of Ti(III)Cl in 20-30% hydrochloric acid. After 21 hours, another 2.0 ml of the Ti(III)Cl solution is added. Renewed additions of the Ti(III)Cl solution are carried out after 4 hours (3.0 ml) or 16 hours (4.0 ml). After another 6 hours, the batch is diluted with ethyl acetate and made basic with 1N NaOH solution. It is filtered on Celite, and the filter cake is washed with ethyl acetate. The organic phase is separated, dried (Na2SO4), filtered and concentrated by evaporation. The residue that is obtained is purified by chromatography (hexane/ethyl acetate 7:3). 290 mg (0.81 mmol, corresponding to 62% of theory) of the product is obtained.

Workup

  1. custom(3.0 ml) or 16 hours (4.0 ml)
  2. waitAfter another 6 hours
  3. filtrationIt is filtered on Celite
  4. washthe filter cake is washed with ethyl acetate
  5. customThe organic phase is separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe residue that is obtained
  10. customis purified by chromatography (hexane/ethyl acetate 7:3)
  11. custom290 mg (0.81 mmol, corresponding to 62% of theory) of the product is obtained

Sources & evidence

ORD record
ord-098002d981784aab8b4c92f8fb64f962
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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