1,2-Dichloroethane → HCID 86690945, compound

HRID 714739Notes

Reaction equation

HRID 714739 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](O)=[O:16])=[C:11]([CH2:18][N:19]2[C:23](=[O:24])[N:22]([CH2:25][C@H:26]([OH:31])[C:27]([F:30])([F:29])[F:28])[C:21]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)=[N:20]2)[CH:10]=1.C1C=CC2N(O)N=[N:45]C=2C=1.C(Cl)CCl.N>CN(C=O)C.O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([NH2:45])=[O:16])=[C:11]([CH2:18][N:19]2[C:23](=[O:24])[N:22]([CH2:25][C@H:26]([OH:31])[C:27]([F:30])([F:29])[F:28])[C:21]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)=[N:20]2)[CH:10]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 222Ammonia2×HCID 757711-HydroxybenzotriazoleHCID 86690946HCID 86690946, compound

Product 1

HCID 86690945HCID 86690945, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

45 mg (0.07 mmol) of the compound from Example 134 were initially charged in 1 ml of DMF, and 13 mg (0.09 mmol) of HOBt and 18 mg (0.09 mmol) of EDC were added. After 10 min of stirring at RT, 80 μl (1.44 mmol) of ammonia solution (35% strength in water) were added, and the mixture was stirred at RT for 16 h. Under reduced pressure, the reaction solution was then freed of excess ammonia, 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 20 mg (46% of theory) of the target compound.

Workup

  1. stirringthe mixture was stirred at RT 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-2f0dcb550cfa4a9cb859c91d75df120f
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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