Dimethyl Sulfoxide → HCID 9870915, compound

HRID 2182015Notes

Reaction equation

HRID 2182015 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:20])=[C:9]([NH:11][C:12]([O:14]CC(Cl)(Cl)Cl)=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C:32]2[CH:33]=[N:34][C:35]([CH2:38][N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[CH:36][CH:37]=2)=[CH:24][CH:23]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:20])=[C:9]([NH:11][C:12]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([C:32]3[CH:33]=[N:34][C:35]([CH2:38][N:39]4[CH2:40][CH2:41][O:42][CH2:43][CH2:44]4)=[CH:36][CH:37]=3)=[CH:24][CH:23]=2)=[O:14])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 102679534-[5-(4-Aminonaphthyl)pyridin-2-ylmethyl]morpholineHCID 12988817HCID 12988817, compound

Product 1

HCID 9870915HCID 9870915, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-t-butyl-2-methyl-1-(2,2,2-trichloroethoxycarbonyl)aminobenzene (26 mmol), 1-amino-4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalene (26 mmol), diisopropylethylamine (3.2 g, 25 mmol) and DMSO (75 mL) is heated to 55-60° C. and held for 1.5 h. To this solution, ethyl acetate (100 mL) is added. The organic layer is washed with brine (4×50 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and residue is crystallized from a suitable solvent such as acetonitrile (50 mL) at 0° C. The product is collected by filtration and recrystallized from a suitable solvent such as isopropanol and dried in vacuum to constant weight.

Workup

  1. washThe organic layer is washed with brine (4×50 mL)
  2. dry with materialdried over MgSO4
  3. customThe solvent is removed under reduced pressure, and residue
  4. customis crystallized from a suitable solvent such as acetonitrile (50 mL) at 0° C
  5. filtrationThe product is collected by filtration
  6. customrecrystallized from a suitable solvent such as isopropanol
  7. customdried in vacuum to constant weight

Sources & evidence

ORD record
ord-645ad98b90c8446ba727a219c5ac6736
Source dataset
uspto-grants-2005_05
Patent number
US06894173B2

Reaction notes

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