2-Furancarbonyl chloride → HCID 117812392, compound

HRID 1481852Notes

Reaction equation

HRID 1481852 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]([N:20]([CH3:22])[CH3:21])=[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>[CH3:21][N:20]([CH3:22])[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

Participants

6

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 117812411HCID 117812411, compound

Product 1

HCID 117812392HCID 117812392, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-dimethylamino-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 7c (91.7 mg, 0.19 mmol, 100 mol %) and N,N-diisopropylethylamine (0.10 ml, 0.58 mmol, 300 mol %) in dichloromethane (4.0 ml) was added furan-2-carbonyl chloride (0.02 ml, 0.23 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 to a residue that was purified by column chromatography (dichloromethane to 10% methanol/dichloromethane) to afford furan-2-carboxylic acid [4-dimethylamino-5-[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide 7d (50.0 mg; 0.09 mmol, 45.6%) 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 to a residue that
  4. customwas purified by column chromatography (dichloromethane to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-13b9188e95924ad3a44309ea28415d0b
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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