1,2-Dichloroethane → HCID 69937008, compound

HRID 1623776Notes

Reaction equation

HRID 1623776 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:14]([CH:18]=2)[C:15](O)=[O:16])=[O:9])[CH2:4][CH2:3]1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([NH2:33])[CH:28]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:14]([CH:18]=2)[C:15]([NH:33][C:29]2[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=2)=[O:16])=[O:9])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 68108650HCID 68108650, compound

Product 1

HCID 69937008HCID 69937008, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[(4-methyl-1-piperazinyl)carbonyl]-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 51; 166 mg, 0.47 mmol), 3-pyridinamine (44.1 mg, 0.47 mmol), and EDC (90 mg, 0.47 mmol) in N,N-dimethylformamide (DMF) (4 mL) stirred under nitrogen at room temperature was added neat HOBT (71.7 mg, 0.47 mmol) in one charge. The reaction mixture was stirred at room temperature for 6 h. The mixture was diluted with water (50 ml), extracted with ethyl acetate (3×50 ml). The organic phase was washed with saturated brine (25 ml), dried over sodium sulfate, and evaporated in vacuo to give the crude product. The crude product was purified by Prep-HPLC (Gilson GX-281; Durashell 10 μm, 21.5*250 nm n; A: 10 mmol/water, B: MeCN, O-7.2 min, 35%-35%; 7.2-7.5 min, 35%-95%; 7.5-11.5 min, 95%; RT: 7.0 min) to yield the title compound as a white solid. 30 mg.

Workup

  1. additioncharge
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe organic phase was washed with saturated brine (25 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customto give the crude product
  7. customThe crude product was purified by Prep-HPLC (Gilson
  8. custom7.2 min, 35%-35%
  9. custom7.2-7.5 min, 35%-95%
  10. custom7.5-11.5 min, 95%

Sources & evidence

ORD record
ord-e7b4f95c88c24fdd9fad0d82cb0ff3f4
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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