Ethanolamine → HCID 18931094, compound

HRID 1599028Notes

Reaction equation

HRID 1599028 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[N:17]=[C:16](S(C)(=O)=O)[N:15]=[C:14]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:13]=1[C:36]1[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].[NH2:45][CH2:46][CH2:47][OH:48]>>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[N:17]=[C:16]([NH:45][CH2:46][CH2:47][OH:48])[N:15]=[C:14]([NH:22][S:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([CH3:33])([CH3:35])[CH3:34])=[CH:30][CH:31]=2)(=[O:25])=[O:24])[C:13]=1[C:36]1[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 25517Ammonium ChlorideHCID 18931092HCID 18931092, compound

Product 1

HCID 18931094HCID 18931094, compound

Conditions

Temperature
120 °C

Procedure

##STR152## (1) A solution of N-[6-(2-benzyloxyethoxy)-5-(4-methylphenyl)-2-methylsulfonylpyrimidin-4-yl]-4-tert-butylbenzenesulfonamide obtained in Reference Example 11-(6) (300 mg) in 2-aminoethanol (4 ml) is heated with stirring at 120° C. for three hours. After cooling, to the reaction solution is added an aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1), and recrystallized from isopropyl ether-n-hexane to give N-[6-{2-benzyloxyethoxy)-2-(2-hydroxyethylamino)-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (260 mg) as a crystal.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling, to the reaction solution
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe ethyl acetate layer is washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1)
  9. customrecrystallized from isopropyl ether-n-hexane

Sources & evidence

ORD record
ord-e9308ab6550d49d48b33ff5e57f4e7a8
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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