Hydrochloric Acid → N-(1-phenylethyl)-[6-(4-t-butylphenylsulfonylamino)-2-(4-formylpiperazinyl)-5-(2-methoxyphenoxy)-4-pyrimidinyloxy]-acetamide

HRID 1418349Notes

Reaction equation

HRID 1418349 reaction equation
[C:1]1([CH:7]([NH:9][C:10](=[O:13])[CH2:11][OH:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].[C:15]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]2[C:34]([O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])=[C:33](Cl)[N:32]=[C:31]([N:45]3[CH2:50][CH2:49][N:48]([CH:51]=[O:52])[CH2:47][CH2:46]3)[N:30]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].Cl>CS(C)=O.O>[C:1]1([CH:7]([NH:9][C:10](=[O:13])[CH2:11][O:12][C:33]2[C:34]([O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])=[C:29]([NH:28][S:25]([C:22]3[CH:21]=[CH:20][C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:24][CH:23]=3)(=[O:27])=[O:26])[N:30]=[C:31]([N:45]3[CH2:50][CH2:49][N:48]([CH:51]=[O:52])[CH2:47][CH2:46]3)[N:32]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 158811362-Hydroxy-N-(1-phenylethyl)acetamideHCID 86753877HCID 86753877, compound

Product 1

HCID 54369531N-(1-phenylethyl)-[6-(4-t-butylphenylsulfonylamino)-2-(4-formylpiperazinyl)-5-(2-methoxyphenoxy)-4-pyrimidinyloxy]-acetamideYield 34%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

N-(1-Phenylethyl)-hydroxyacetamide (50 mg, 0.3 mmol) was dissolved in dimethyl sulfoxide (0.56 ml). Sodium (11.5 mg; 0.5 mmol) was added to the solution, and the resultant mixture was stirred at room temperature for two hours. 4-t-Butyl-N-[6-chloro-2-(4-formylpiperazinyl)-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide (56 mg; 0.1 mmol) was added thereto, and the resultant mixture was stirred for 1 hour at 120° C., then poured into water, made acidic with hydrochloric acid, and extracted with ethyl acetate. The extracted was washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1), to thereby obtain 23.8 mg (yield: 34%) of the title compound as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracted was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-559b74be91e24d098c32abd467ab3f47
Source dataset
uspto-grants-1999_03
Patent number
US05883092

Reaction notes

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