2-Dimethylaminopyridine → HCID 19087764, compound

HRID 1464378Notes

Reaction equation

HRID 1464378 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21](O)=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.[CH3:24][S:25]([NH2:28])(=[O:27])=[O:26].Cl.C(N=C=NCCCN(C)C)C.CN(C1C=CC=CN=1)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([CH2:24][S:25]([NH2:28])(=[O:27])=[O:26])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19087795HCID 19087795, compound

Product 1

HCID 19087764HCID 19087764, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6 g (0.019 mol) of the compound from Example XV, 1.9 g (0.019 mol) of dried methanesulphonamide, 3.8 g (0.019 mol) of N-ethyl-N'-dimethylaminopropylcarbodiimide hydrochloride and 2.4 g (0.019 mol) of dimethylaminopyridine are dissolved in 40 ml of dichloromethane and the mixture is stirred at room temperature for 60 h. It is then evaporated to dryness in vacuo, the residue is taken up in 40 ml of dichloromethane and the solution is washed twice with 20 ml of water. After drying the organic phase using Na2SO4, it is evaporated in vacuo and the residue is separated by column chromatography (silica gel 60, eluent dichloromethane/ethyl acetate/glacial acetic acid=10:1:1).

Workup

  1. customIt is then evaporated to dryness in vacuo
  2. washthe solution is washed twice with 20 ml of water
  3. customAfter drying the organic phase
  4. customis evaporated in vacuo
  5. customthe residue is separated by column chromatography (silica gel 60, eluent dichloromethane/ethyl acetate/glacial acetic acid=10:1:1)

Sources & evidence

ORD record
ord-290a4a83415742d8a42219eb82c4d0aa
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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