Dimethylamine → HCID 15238188, compound

HRID 1728776Notes

Reaction equation

HRID 1728776 reaction equation
Cl.[NH2:2][CH:3]([C:14](=[O:31])[CH2:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1)[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.Cl[CH2:33][CH2:34][CH2:35][CH2:36][C:37](Cl)=[O:38].[CH3:40][NH:41][CH3:42].[I-].[K+]>ClCCl.C(O)C.C(N(CC)CC)C>[F:30][C:27]([F:28])([F:29])[C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][C:14](=[O:31])[CH:3]([NH:2][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][N:41]([CH3:42])[CH3:40])[CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)[CH:22]=[C:21]([C:23]([F:25])([F:24])[F:26])[CH:20]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 4875Potassium IodideHCID 740895-Chlorovaleryl chlorideHCID 22905844HCID 22905844, compound

Product 1

HCID 15238188HCID 15238188, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution containing the compound of Example 11 (1.1 g) in dichloromethane (50 ml) was treated with chlorovaleryl chloride (0.52 ml) and triethylamine (0.64 ml) for 16 hours. The reaction was diluted with dichloromethane, washed with dilute hydrochloric acid and aqueous sodium bicarbonate, dried (Na2SO4) and concentrated to give an oil. To a solution containing the forgoing oil in ethanol (5 ml) was added dimethylamine (5 ml of a 33% solution in ethanol) and potassium iodide (50 mg). After stirring for 4 days the mixture was partitioned between ethyl acetate and water. The ethyl acetate solution was separated, dried and concentrated and the residue purified by chromatography on silica gel eluting with ethyl acetate-methanol (95:5) to give the title compound, mp 140° C.; found: C, 59.31; H, 5.47; N, 7.37. C28H31F6N3O.0.5H2O requires: C, 59.57; H, 5.71; N, 7.44.

Workup

  1. washwashed with dilute hydrochloric acid and aqueous sodium bicarbonate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto give an oil
  5. customwas partitioned between ethyl acetate and water
  6. customThe ethyl acetate solution was separated
  7. customdried
  8. concentrationconcentrated
  9. customthe residue purified by chromatography on silica gel eluting with ethyl acetate-methanol (95:5)

Sources & evidence

ORD record
ord-b2e3f51653a64560a37b126ade2d559b
Source dataset
uspto-grants-1994_07
Patent number
US05328927

Reaction notes

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