1,2-Dichloroethane → HCID 86690917, compound

HRID 714687Notes

Reaction equation

HRID 714687 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([CH2:13][C:14](O)=[O:15])[N:11]=[C:10]([CH2:17][N:18]2[C:22](=[O:23])[N:21]([CH2:24][C@H:25]([OH:30])[C:26]([F:29])([F:28])[F:27])[C:20]([C:31]3[CH:36]=CC(Cl)=[CH:33][CH:32]=3)=[N:19]2)[N:9]=1.C1C=CC2N(O)N=[N:44]C=2C=1.[CH2:48]([Cl:51])[CH2:49]Cl.N>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([CH2:13][C:14]([NH2:44])=[O:15])[N:11]=[C:10]([CH2:17][N:18]2[C:22](=[O:23])[N:21]([CH2:24][C@H:25]([OH:30])[C:26]([F:27])([F:28])[F:29])[C:20]([C:31]3[CH:36]=[CH:49][C:48]([Cl:51])=[CH:33][CH:32]=3)=[N:19]2)[N:9]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 222Ammonia2×HCID 757711-HydroxybenzotriazoleHCID 53378731HCID 53378731, compound

Product 1

HCID 86690917HCID 86690917, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

54 mg (0.10 mmol) of the compound from Example 60 were initially charged in 4 ml of DMF, and 19 mg (0.13 mmol) of HOBt and 24 mg (0.03 mmol) of EDC were added. After 10 min of stirring at RT, 0.1 ml (1.93 mmol) of ammonia solution (32% strength in water) were added and the mixture was stirred at room temperature for 16 h. The reaction solution was then freed from excess ammonia under reduced pressure, about 3 ml of water were added and the mixture was extracted three times with in each case 5 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 27 mg (46% of theory) of the target compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. additionwere added
  3. extractionthe mixture was extracted three times with in each case 5 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-af7577b7cde84253a79a94f6c8aee8e7
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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