Ethyl Acetate → HCID 59020365, compound

HRID 970441Notes

Reaction equation

HRID 970441 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[OH-].[Na+].C(OCC)(=O)C>C1COCC1.Cl>[NH2:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[C:15]([NH:14][CH2:13][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)=[O:25]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 17986387HCID 17986387, compound

Product 1

HCID 59020365HCID 59020365, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 568 mg (1.32 mmol) of N-[4-(5-bromo-2-chloro-pyrimidin-4-ylamino)-butyl]-3-nitro-benzamide in 15 ml of THF is mixed at room temperature with 9 ml of a 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid. After 21 hours, the batch is made basic with 2N NaOH solution, mixed with ethyl acetate and filtered on Celite. The filter cake is rewashed with ethyl acetate. The organic phase of the filtrate is filtered through a Whatman filter and concentrated by evaporation. 447 mg (1.12 mmol, corresponding to 85% of theory) of the product is obtained.

Workup

  1. filtrationfiltered on Celite
  2. filtrationThe organic phase of the filtrate is filtered through a Whatman
  3. filtrationfilter
  4. concentrationconcentrated by evaporation
  5. custom447 mg (1.12 mmol, corresponding to 85% of theory) of the product is obtained

Sources & evidence

ORD record
ord-774617669d7244ef9fc4da52ffc9b20c
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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