1,2-Dichloroethane → HCID 11526310, compound

HRID 1787948Notes

Reaction equation

HRID 1787948 reaction equation
[NH2:1][CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:27])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1.[Cl:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH:12]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([NH:6][CH2:5][C:4]#[C:3][CH2:2][NH:1][C:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:29]([Cl:28])=[CH:30][CH:31]=2)=[O:27])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 63184-Chlorobenzoic AcidHCID 57602573HCID 57602573, compound

Product 1

HCID 11526310HCID 11526310, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,6-bis-(4-fluoro-phenyl)-hexanoic acid (4-amino-but-2-ynyl)-amide (0.69 g, 1.86 mmol) in dry CH2Cl2 (40 ml) was added 4-chlorobenzoic acid (0.29 g, 1.86 mmol) under nitrogen. To the reaction was added EDC (0.71 g, 3.72 mmol) and DMAP (cat) and the reaction mixture stirred under nitrogen at room temperature overnight. The reaction was then concentrated under reduced pressure. The residue dissolved in ethyl acetate: water (10:1) (150 ml). The organic was washed with water (30 ml, 2×) and 10% NaOH (30 ml) and dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using CH2Cl2:CH3OH (20:1) to give a desired product in good yield.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutionThe residue dissolved in ethyl acetate: water (10:1) (150 ml)
  3. washThe organic was washed with water (30 ml, 2×) and 10% NaOH (30 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-9cdc826fca4742448ad1df9f3e7630f6
Source dataset
uspto-grants-2009_03
Patent number
US07511077B2

Reaction notes

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