3-(tert-Butylamino)propane-1,2-diol → 1-Tert.butylamino-3-(2-methyl-4-thieno[3,2-c]pyridinyloxy)-2-propanol

HRID 1973675Notes

Reaction equation

HRID 1973675 reaction equation
[K].[C:2]([NH:6][CH2:7][CH:8]([OH:11])[CH2:9][OH:10])([CH3:5])([CH3:4])[CH3:3].Cl[C:13]1[C:18]2[CH:19]=[C:20]([CH3:22])[S:21][C:17]=2[CH:16]=[CH:15][N:14]=1>C(O)(C)(C)C>[C:2]([NH:6][CH2:7][CH:8]([OH:11])[CH2:9][O:10][C:13]1[C:18]2[CH:19]=[C:20]([CH3:22])[S:21][C:17]=2[CH:16]=[CH:15][N:14]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 908313-(tert-Butylamino)propane-1,2-diolHCID 5462222PotassiumHCID 181763724-Chloro-2-methylthieno[3,2-c]pyridine

Product 1

HCID 214903061-Tert.butylamino-3-(2-methyl-4-thieno[3,2-c]pyridinyloxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

0.49 g of potassium are dissolved with heating in 60 cc of tert.butanol. After cooling, 1.5 g of 1-tert.butylamino-2,3-dihydroxypropane was added and subsequently 1.85 g of 4-chloro-2-methylthieno[3,2-c]pyridine was added. After stirring for one day at room temperature, heating is effected to 50° for a further day. The reaction solution is concentrated in a vacuum, the residue is taken up in 1 N hydrochloric acid and ether, the aqueous phase is neutralized with 2 N soda solution and extracted with methylene chloride. After drying over magnesium sulphate and concentrating, the title compound is obtained as an oil, which yields the hydrogen maleate having an M.P. of 210°-213°, with maleic acid in tetrahydrofuran.

Workup

  1. temperatureAfter cooling
  2. temperatureheating
  3. waitis effected to 50° for a further day
  4. concentrationThe reaction solution is concentrated in a vacuum
  5. extractionextracted with methylene chloride
  6. dry with materialAfter drying over magnesium sulphate
  7. concentrationconcentrating

Sources & evidence

ORD record
ord-52175175aa0b41a587499117a18b032b
Source dataset
uspto-grants-1976_12
Patent number
US03998835

Reaction notes

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