Sodium Hydroxide → HCID 17986365, compound

HRID 970427Notes

Reaction equation

HRID 970427 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][NH:12][S:13]([C:16]2[S:17][CH:18]=[C:19]([N+:21]([O-])=O)[CH:20]=2)(=[O:15])=[O:14])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.BrC1C(NCCNS(C2SC([N+]([O-])=O)=CC=2)(=O)=O)=NC(Cl)=NC=1.[OH-].[Na+]>C1COCC1.Cl>[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][NH:12][S:13]([C:16]2[S:17][CH:18]=[C:19]([NH2:21])[CH:20]=2)(=[O:14])=[O:15])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 17986381HCID 17986381, compoundHCID 17986390HCID 17986390, compound

Product 1

HCID 17986365HCID 17986365, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 600 mg (1.35 mmol) of a mixture of 4-nitro-thiophene-2-sulfonic acid [2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-ethyl]-amide and 5-nitro-thiophene-2-sulfonic acid-[2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-ethyl]-amide (ratio 10/6) in 40 ml of THF is mixed under argon at room temperature with 6.4 ml of a 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid. After 46 hours, the reaction solution is mixed again with 2.0 ml of Ti(III)Cl solution and stirred for another 7 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 filtered through a Whatman filter and concentrated by evaporation. The residue is purified by chromatography (hexane/ethyl acetate 1:4). 178 mg (0.43 mmol, corresponding to 32% 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. filtrationThe combined organic phases are filtered through a Whatman
  5. filtrationfilter
  6. concentrationconcentrated by evaporation
  7. customThe residue is purified by chromatography (hexane/ethyl acetate 1:4)
  8. custom178 mg (0.43 mmol, corresponding to 32% of theory) of the product is obtained

Sources & evidence

ORD record
ord-8c5b6d8bfb4e4f85a88d95b1306c91d8
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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