1-Butanol → HCID 21923072, compound

HRID 1272655Notes

Reaction equation

HRID 1272655 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:14])[CH2:12][CH3:13])=[C:4](Cl)[N:3]=1.C(O)CCC.[F:21][C:22]([F:32])([F:31])[O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1>C(O)(C)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:14])[CH2:12][CH3:13])=[C:4]([NH:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][C:22]([F:21])([F:31])[F:32])=[CH:25][CH:26]=2)[N:3]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 6008484-(Trifluoromethoxy)anilineHCID 21922929HCID 21922929, compound

Product 1

HCID 21923072HCID 21923072, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The operation is carried out as in Stage 2 of Example 9 starting from 200 mg of the product obtained in Stage 1 of Example 9 and 4 ml of butanol and using 0.135 ml of 4-(trifluoromethoxy)-benzenamine in place of the benzylamine. Agitation is carried out at ambient temperature then the reaction medium is taken to a temperature of 80 to 85° C. for approximately 22 hours, left to return to ambient temperature, diluted with 4 ml of isopropanol and placed for two days at a temperature of approximately 0° C., followed by separating, washing with 5 ml of isopropanol and drying at a temperature of approximately 50° C. After purification on silica eluting with methylene chloride/ethyl acetate in a proportion of 90/10, 210 mg of expected product is obtained in the form of white crystals.

Workup

  1. customis carried out at ambient temperature
  2. waitleft
  3. customto return to ambient temperature
  4. waitplaced for two days at a temperature of approximately 0° C.
  5. customby separating
  6. washwashing with 5 ml of isopropanol
  7. customdrying at a temperature of approximately 50° C
  8. customAfter purification on silica eluting with methylene chloride/ethyl acetate in a proportion of 90/10

Sources & evidence

ORD record
ord-85298f7ba2d1456ab2caac64c6a89071
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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