Iodoethane → HCID 178463666, compound

HRID 1422746Notes

Reaction equation

HRID 1422746 reaction equation
[CH2:1](I)[CH3:2].[O:4]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][NH:15][C@H:16]3[CH2:21][CH2:20][C@H:19]([CH2:22][O:23][C:24]([C:26]4[CH:27]=[N:28][C:29]5[C:34]([CH:35]=4)=[CH:33][C:32]([O:36][CH3:37])=[CH:31][CH:30]=5)=[O:25])[CH2:18][CH2:17]3)=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1>CN(C)C=O.[Ag]=O>[O:4]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][N:15]([CH2:1][CH3:2])[C@H:16]3[CH2:21][CH2:20][C@H:19]([CH2:22][O:23][C:24]([C:26]4[CH:27]=[N:28][C:29]5[C:34]([CH:35]=4)=[CH:33][C:32]([O:36][CH3:37])=[CH:31][CH:30]=5)=[O:25])[CH2:18][CH2:17]3)=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 178487901HCID 178487901, compound

Product 1

HCID 178463666HCID 178463666, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

Ethyl iodide (51 μL, 0.63 mmol, 8.0 eq) is added at room temperature to a stirred solution of 6-methoxy-quinoline-3-carboxylic acid trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amino]-cyclohexylmethyl ester (37 mg, 0.08 mmol, 1.0 eq) in N,N-dimethylformamide (0.5 mL), followed by silver oxide (73 mg, 0.31 mmol, 4.0 eq). After 4 hours stirring at room temperature, the reaction mixture is filtered through decalite and the mother liquid is concentrated to give a residue that is purified by preparative HPLC to afford 6-methoxy-quinoline-3-carboxylic acid trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-ethyl-amino]-cyclohexylmethyl ester as an off-white lyophilizated solid (9 mg, 14% yield)

Workup

  1. filtrationthe reaction mixture is filtered through decalite
  2. concentrationthe mother liquid is concentrated
  3. customto give a residue that
  4. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-d97d2c0772174d17b1afb9b18ca81532
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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