Methylamine → HCID 53883593, compound

HRID 2226534Notes

Reaction equation

HRID 2226534 reaction equation
CS(Cl)(=O)=O.[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[Cl:16])[C@@H:12]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[C@H:11](O)[CH2:10]2.[CH2:23]([N:25](CC)CC)C.CN>O1CCCC1.C(O)C>[Cl:16][C:15]1[CH:14]=[C:10]2[C:9](=[CH:8][C:7]=1[Cl:6])[C@@H:13]([NH:25][CH3:23])[C@H:12]([N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)[CH2:11]2

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54091718HCID 54091718, compound

Product 1

HCID 53883593HCID 53883593, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of 17 ml of methane sulfonyl chloride in 3 ml of tetrahydrofuran was added dropwise at -20° C. to a mixture of 5 g of the product of Step E, 40 ml of tetrahydrofuran and 4 ml of triethylamine and after stirring for 15 minutes at -20° C., the temperature was raised to 0° C. and 20 ml of methylamine in ethanol were added. The mixture was stirred for 22 hours and was evaporated to dryness. The residue was diluted with water and after the addition of a few drops of sodium hydroxide solution, the mixture was extracted with ethyl acetate. The organic phase was washed with aqueous sodium chloride solution, dried and evaporated to dryness under reduced pressure to obtain 5.7 g of residue. The latter was chromatographed on silica and eluted with a 8-1-1 ethyl acetate-methanol-triethylamine mixture and after standing at 4° C., 4.91 g of the desired crystalline product melting at ≈55° C. were obtained.

Workup

  1. temperaturethe temperature was raised to 0° C.
  2. stirringThe mixture was stirred for 22 hours
  3. customwas evaporated to dryness
  4. additionThe residue was diluted with water
  5. additionafter the addition of a few drops of sodium hydroxide solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with aqueous sodium chloride solution
  8. customdried
  9. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-89a53de1799b4b3b889af61bb3746c9f
Source dataset
uspto-grants-1994_09
Patent number
US05348971

Reaction notes

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