Diisopropylamine → HCID 66634914, compound

HRID 510058Notes

Reaction equation

HRID 510058 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:3]=1.[CH3:28][O:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33].C(NC(C)C)(C)C>O1CCOCC1>[CH3:28][O:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:31]=1[CH2:32][NH:33][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 5972502,4-DimethoxybenzylamineHCID 86720047HCID 86720047, compound

Product 1

HCID 66634914HCID 66634914, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

15.00 g (38.99 mmol) of the compound from example 79A were dissolved in 200 ml of dioxane, 6.98 g (40.94 mmol) of 2,4-dimethoxybenzylamine and 5.54 g (42.88 mmol) of N,N-diisopropylamine were added and the mixture was stirred at 85° C. for 1 h. After cooling, the mixture was filtered and the filtrate was concentrated on a rotary evaporator and the residue was dried under high vacuum. The residue was crushed with a mortar and pestle, stirred with 250 ml of water, filtered off with suction and dried under high vacuum. 19.96 g (89% of theory) of the title compound were obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated on a rotary evaporator
  4. customthe residue was dried under high vacuum
  5. customThe residue was crushed with a mortar and pestle
  6. stirringstirred with 250 ml of water
  7. filtrationfiltered off with suction
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-4eac70db3a9c476abba2cffab7d7b5a6
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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