1,2-Dichloroethane → HCID 58802849, compound

HRID 14326

Reaction equation

HRID 14326 reaction equation
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:27][CH:28]([CH2:42][C:43]1[CH:48]=[C:47]([F:49])[CH:46]=[C:45]([F:50])[CH:44]=1)[CH:29]([OH:41])[CH2:30][NH:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH3:40])[CH:34]=1>CN(C=O)C>[F:49][C:47]1[CH:48]=[C:43]([CH:44]=[C:45]([F:50])[CH:46]=1)[CH2:42][C@H:28]([NH:27][C:1]([C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1)=[O:12])[C@H:29]([OH:41])[CH2:30][NH:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH3:40])[CH:34]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 71961,3-Benzodioxole-5-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 218657313-Amino-4-(3,5-difluoro-phenyl)-1-(3-ethyl-benzylamino)-butan-2-ol

Product 1

HCID 58802849HCID 58802849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of piperonylic acid (0.500 g, 3.01 mmol), EDC (0.867 g, 4.52 mmol), HOBT (0.611 g, 4.52 mmol) in anhydrous DMF (10 mL) was added a solution of TEA (1.67 mL, 12.04 mmol), 3-Amino-4-(3,5-difluoro-phenyl)-1-(3-ethyl-benzylamino)-butan-2-ol (1.693 g, 3.01 mmol), and anhydrous DMF (5 mL). Reaction mixture was stirred under nitrogen overnight. Quenched reaction mixture with 10% sodium bicarbonate (aq.) then extracted with ethyl acetate. Washed organic layer with 1N HCl, followed by a wash with 10% sodium bicarbonate (aq.). Dried organic layer over magnesium sulfate, filtered, then concentrated in vacuo, yielding the product. (ES+: 483.2)

Workup

  1. customReaction mixture
  2. customQuenched
  3. customreaction mixture with 10% sodium bicarbonate (aq.)
  4. extractionthen extracted with ethyl acetate
  5. washa wash with 10% sodium bicarbonate (aq.)
  6. filtrationDried organic layer over magnesium sulfate, filtered
  7. concentrationconcentrated in vacuo
  8. customyielding the product

Sources & evidence

ORD record
ord-72a4e100a2094b9b86fc071a0eb2c159
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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