Methylamine → HCID 57980010, compound

HRID 1867549Notes

Reaction equation

HRID 1867549 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=3)=[CH:11][CH:10]=2)[C:5](=[O:23])[CH2:4][O:3]1.[CH3:24][NH2:25]>CO.O1CCCC1>[C:21]([C:17]1[CH:16]=[C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][NH:6][C:2](=[O:1])[O:3][CH2:4][C:5]([NH:25][CH3:24])=[O:23])=[CH:14][CH:13]=2)[CH:20]=[CH:19][CH:18]=1)#[N:22]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 67528824HCID 67528824, compound

Product 1

HCID 57980010HCID 57980010, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (6.53 mmol) of 4′-[2-(2,4-dioxo-1,3-oxazolidin-3-yl)ethyl]-3-biphenylcarbonitrile, prepared in step 11.2., are dissolved in a mixture of 13 ml of methanol and 9.8 ml of a 2N solution of methylamine (19.6 mmol) in tetrahydrofuran. The solution is left to react overnight and then evaporated to dryness and the residue is purified by chromatography on silica gel, eluting with a 96/4 then 95/5 mixture of dichloromethane and methanol. The product is recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 1.07 g of product in the form of a white powder.

Workup

  1. waitThe solution is left
  2. customto react overnight
  3. customevaporated to dryness
  4. customthe residue is purified by chromatography on silica gel
  5. washeluting with a 96/4
  6. addition95/5 mixture of dichloromethane and methanol
  7. customThe product is recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-546df0c62f1847e78f2676034e590954
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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