Sodium Hydroxide → HCID 59020422, compound

HRID 970421Notes

Reaction equation

HRID 970421 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[C:19]([N+:26]([O-:28])=[O:27])[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:21]1[CH:22]=[C:17]([S:14]([NH: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)(=[O:15])=[O:16])[CH:18]=[C:19]([N+:26]([O-:28])=[O:27])[CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 17986394HCID 17986394, compound

Product 1

HCID 59020422HCID 59020422, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 602 mg (1.28 mmol) of N-[3-(5-bromo-2-chloro-pyrimidin-4-ylamino)-propyl]-3,5-dinitro-benzenesulfonamide in 10 ml of THF is mixed at room temperature with 4.2 ml of a 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid. After 2 hours, it is mixed again with 3.0 ml of a 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid, and it is stirred for another 16 hours. The batch is made basic with 2N NaOH solution and filtered. The filter cake is rewashed with THF and water. The THF of the filtrate is drawn off on a rotary evaporator, and the residue is extracted from ethyl acetate. The combined organic phases are filtered through a Whatman filter and concentrated by evaporation. 440 mg (0.95 mmol, corresponding to 74% of theory) of the product is obtained.

Workup

  1. filtrationfiltered
  2. customThe THF of the filtrate is drawn off on a rotary evaporator
  3. extractionthe residue is extracted from ethyl acetate
  4. filtrationThe combined organic phases are filtered through a Whatman
  5. filtrationfilter
  6. concentrationconcentrated by evaporation
  7. custom440 mg (0.95 mmol, corresponding to 74% of theory) of the product is obtained

Sources & evidence

ORD record
ord-6288fabec59447a0a99e96050f5437c2
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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