Diisopropylethylamine → HCID 10116750, compound

HRID 395357Notes

Reaction equation

HRID 395357 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:24][NH2:25])[N:13]=2)=[O:11])=[CH:5][CH:4]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35](Cl)=[O:36])=[CH:30][CH:29]=1.CCN(C(C)C)C(C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:24][NH:25][C:35](=[O:36])[CH2:34][C:31]3[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)[N:13]=2)=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 22345549HCID 22345549, compound

Product 1

HCID 10116750HCID 10116750, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

39 mg (0.12 mmol) of 6-(2-Aminomethylphenyl)-pyridine-2-carboxylic acid-(4-methoxyphenyl)-amide were dissolved in 3 ml of dichloromethane, treated with 27 μl (0.144 mmol) of 4-methoxyphenylacetyl chloride and 19 mg (0.144 mmol) of DIPEA and the mixture was stirred overnight. It was diluted with 20 ml of dichloromethane and washed with an NaHCO3 solution. The organic phase was dried, concentrated and purified by RP-HPLC. 56 mg (78%) of the compound of Example 20 were obtained in the form of its trifluoroacetate.

Workup

  1. washwashed with an NaHCO3 solution
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-f6a72a0c3d48450ca033a57ab7a498ba
Source dataset
uspto-grants-2003_08
Patent number
US06605625B2

Reaction notes

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