2-Furancarbonyl chloride → HCID 89692935, compound

HRID 1481855Notes

Reaction equation

HRID 1481855 reaction equation
[NH2:1][C:2]1[C:3]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:25][CH2:24]2)=[CH:4][C:5]([O:20][CH2:21][CH3:22])=[C:6]([CH:19]=1)[C:7]([NH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])=[O:8].C(N(CC)C(C)C)(C)C.[O:45]1[CH:49]=[CH:48][CH:47]=[C:46]1[C:50](Cl)=[O:51]>ClCCl.O>[CH2:21]([O:20][C:5]1[C:6]([C:7](=[O:8])[NH:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])=[CH:19][C:2]([NH:1][C:50]([C:46]2[O:45][CH:49]=[CH:48][CH:47]=2)=[O:51])=[C:3]([N:23]2[CH2:24][CH2:25][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:27][CH2:28]2)[CH:4]=1)[CH3:22]

Participants

6

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 89690637HCID 89690637, compound

Product 1

HCID 89692935HCID 89692935, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-ethoxy-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 8c (44.8 mg, 0.09 mmol, 100 mol %) and N,N-diisopropylethylamine (0.05 ml, 0.28 mmol, 300 mol %) in dichloromethane (2.0 ml) was added furan-2-carbonyl chloride (0.01 ml, 0.11 mmol, 120 mol %) and a catalytic amount of N,N-dimethylaminopyridine. The reaction was stirred for 16 h at room temperature and then diluted with water and extracted three times with dichloromethane. The combined organics were dried over sodium sulfate and concentrated and the residue was purified by column chromatography (dichloromethane to 10% methanol/dichloromethane) to afford furan-2-carboxylic acid [4-ethoxy-5-[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide 8g (30.7 mg, 0.05 mmol, 53.6%) as an off-white solid.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography (dichloromethane to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-cee25cf4870045da8deba7398938708f
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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