1,2-Dichloroethane → HCID 66611817, compound

HRID 2204721Notes

Reaction equation

HRID 2204721 reaction equation
[Br:1][C:2]1[C:3]([CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)CCl.ON1C2N=CC=CC=2N=N1.[Cl:40][C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][CH:47]=1)[NH2:44].CCN(C(C)C)C(C)C>CN(C)C=O>[CH2:12]([O:11][C:5]1[CH:4]=[C:3]([CH2:19][N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:2]([Br:1])=[CH:10][C:6]=1[C:7]([NH:44][C:43]1[CH:45]=[CH:46][CH:47]=[C:41]([Cl:40])[CH:42]=1)=[O:8])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79323-ChloroanilineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66611285HCID 66611285, compound

Product 1

HCID 66611817HCID 66611817, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-Bromo-4-(4-morpholinylmethyl)-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in D7) (1 g, 2.461 mmol) in N,N-Dimethylformamide (DMF) (20 mL) was added EDC (0.849 g, 4.43 mmol), 1-hydroxy-7-azabenzotriazole (0.503 g, 3.69 mmol), 3-chloroaniline (0.504 mL, 4.92 mmol), DIPEA (0.860 mL, 4.92 mmol) and the mixture was stirred at room temperature overnight. The DMF was removed on a buchi under reduced pressure, the residue was taken up into DCM (50 ml) and washed with water (2×20 ml). The DCM was evaporated on a buchi under reduced pressure and the residue was purified using the Companion eluting with 0-50% ethyl acetate/cyclohexane to give the title compound as pale yellow oil which solidified on standing. Yield: 400 mg

Workup

  1. customThe DMF was removed on a buchi under reduced pressure
  2. washwashed with water (2×20 ml)
  3. customThe DCM was evaporated on a buchi under reduced pressure
  4. customthe residue was purified
  5. washeluting with 0-50% ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-5ead12cbda374f64ab3e4e118c11c0e1
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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