Ammonium Acetate → HCID 67412584, compound

HRID 714697Notes

Reaction equation

HRID 714697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][CH2:21][C:22](=O)[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=O)[N:9]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:39]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]3[NH:39][C:22]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=4)=[CH:21][N:20]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517165Ammonium Acetate2×HCID 69940334HCID 69940334, compound

Product 1

HCID 67412584HCID 67412584, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

50 mg (0.10 mmol) of the compound from Example 27A were dissolved in 1 ml of DMF and mixed with 23 mg (0.30 mmol) of ammonium acetate, and the mixture was stirred in a microwave oven at 200° C. for 15 min. After cooling, a further 30 mg (0.39 mmol) of ammonium acetate were added, and the mixture was stirred in a microwave oven at 200° C. for another 30 min. After cooling to RT, the mixture was partitioned between 10 ml of ethyl acetate and 10 ml of water. The organic phase was separated off, washed with in each case 10 ml of water and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC [Method 19]. This gave 17 mg (35% of theory) of the target compound as a yellowish resin.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture was stirred in a microwave oven at 200° C. for another 30 min
  3. temperatureAfter cooling to RT
  4. customthe mixture was partitioned between 10 ml of ethyl acetate and 10 ml of water
  5. customThe organic phase was separated off
  6. washwashed with in each case 10 ml of water and saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by preparative HPLC [Method 19]

Sources & evidence

ORD record
ord-5dc0eeb2a8354747b52a12455d4fbdf6
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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