HCID 13922753, compound → HCID 58188811, compound

HRID 1625116Notes

Reaction equation

HRID 1625116 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9](=O)[CH:10]=[C:11]([NH:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([F:25])[CH:16]=2)SC)[CH:5]=[CH:4][N:3]=1.[NH:27]([CH2:29][CH2:30][C:31]([N:33]([CH3:35])[CH3:34])=[O:32])[NH2:28]>CC(O)(C)C>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[N:27]([CH2:29][CH2:30][C:31]([N:33]([CH3:35])[CH3:34])=[O:32])[N:28]=[C:11]([NH:14][C:15]3[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([F:25])[CH:16]=3)[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 13922753HCID 13922753, compoundHCID 76719712HCID 76719712, compound

Product 1

HCID 58188811HCID 58188811, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

D6 (prepared according to Description 6) (1.0 g; 2.48 mmol) was added to a mixture of 3-hydrazinyl-N,N-dimethylpropanamide (0.65 g; 4.95 mmol) in t-BuOH (20 ml) and the reaction mixture stirred at 150° C. for 16 h. The solvent was then evaporated in vacuo and the residue purified by flash chromatography over silica gel (Biotage flash purification system: gradient acetone/heptane from 20/80 to 50/50). The solvent was then evaporated in vacuo and two fractions were collected. The desired fraction yielded 0.40 g of E1 (34.3%).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe residue purified by flash chromatography over silica gel (Biotage flash purification system: gradient acetone/heptane from 20/80 to 50/50)
  3. customThe solvent was then evaporated in vacuo and two fractions
  4. customwere collected

Sources & evidence

ORD record
ord-25745ecb0783429f9e3eb90ee6dc2a52
Source dataset
uspto-grants-2014_07
Patent number
US08779158B2

Reaction notes

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