Sodium Hydroxide → HCID 86630921, compound

HRID 220116Notes

Reaction equation

HRID 220116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[CH2:26][C:25](=[N:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][N:34]([CH2:41][CH2:42][S:43]([CH3:46])(=[O:45])=[O:44])C(=O)C(F)(F)F)[CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.[OH-].[Na+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[CH2:26][C:25](=[N:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][CH2:41][CH2:42][S:43]([CH3:46])(=[O:44])=[O:45])[CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86630919HCID 86630919, compound

Product 1

HCID 86630921HCID 86630921, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 2.6 ml of a mixture (1:1) of tetrahydrofuran and methanol was dissolved 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(4 (N-(2-(methanesulfonyl)ethyl)-2,2,2-trifluoroacetamido)butyloxyimino)quinazoline (V-14, 40 mg), and 86 μl of 1 mol/L aqueous sodium hydroxide solution was added, followed by stirring at room temperature for 14 hours, and at 40° C. for 2 hour. After the reaction, the reaction mixture was extracted with ethyl acetate, the organic layer was dried, and filtrate was concentrated. The concentrated residue was purified by chromatography (eluting with 0 to 3% methanol-contenting ethyl acetated) using an amino column, and the resulting pale yellow oil was powdered with a mixture of hexane and ethyl acetate to obtain 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(4-(2-(methanesulfonyl)ethylamino)butyloxyimino)quinazoline (V-15, 12 mg) as a pale yellow solid.

Workup

  1. additionwas added
  2. waitat 40° C. for 2 hour
  3. customAfter the reaction
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. customthe organic layer was dried
  6. concentrationfiltrate was concentrated
  7. customThe concentrated residue was purified by chromatography (eluting with 0 to 3% methanol-contenting ethyl acetated)
  8. additionthe resulting pale yellow oil was powdered with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-c7e209332e494813b15ce12297b9569e
Source dataset
uspto-grants-2012_06
Patent number
US08202879B2

Reaction notes

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