Hydrochloric Acid → HCID 18327348, compound

HRID 613361Notes

Reaction equation

HRID 613361 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19](Cl)[N:18]=[C:17]([C:31]3[N:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:33]([O:39][CH3:40])[N:32]=3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:37][CH2:35][CH2:34][CH2:33][OH:39])[N:18]=[C:17]([C:31]3[N:36]=[C:35]([O:37][CH2:38][CH2:22][CH2:23][OH:28])[CH:34]=[C:33]([O:39][CH2:40][CH2:19][CH2:20][OH:21])[N:32]=3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18327355HCID 18327355, compound

Product 1

HCID 18327348HCID 18327348, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-t-butyl-N-[6-chloro-2-(4,6-dimethoxy-2-pyrimidinyl)-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide (409 mg) in anhydrous dimethylformamide (2.4 ml) was added dropwise to the above mixture while being cooled on ice. The resultant mixture was stirred for 3.5 hours at 60° C. The reaction mixture was poured into cold 1N HCl, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=20/1) to give obtain 4-t-butyl-N-[2-(4,6-di(3-hydroxypropyloxy)-2-pyrimidinyl)-6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide (250 mg) as a colorless oil.

Workup

  1. temperaturewhile being cooled on ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=20/1)
  7. customto give

Sources & evidence

ORD record
ord-12dd9dbdab604bee9bc3f09985fcf289
Source dataset
uspto-grants-1999_12
Patent number
US06008224

Reaction notes

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