Dichloromethane → HCID 89692973, compound

HRID 1481878Notes

Reaction equation

HRID 1481878 reaction equation
[NH2:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[CH2:14][CH2:13]2)=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.ClCCl.[CH:28]([N:31]([CH2:35][CH3:36])[CH:32](C)C)(C)C.[O:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[C:42](Cl)=[O:43]>>[Cl:11][C:5]1[C:6]([C:7](=[O:9])[NH:15][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[C:36]([CH2:35][N:31]([CH3:28])[CH3:32])[CH:24]=2)=[CH:10][C:2]([NH:1][C:42]([C:38]2[O:37][CH:41]=[CH:40][CH:39]=2)=[O:43])=[C:3]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[CH2:16][CH2:17]2)[CH:4]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 89690464HCID 89690464, compound

Product 1

HCID 89692973HCID 89692973, compound

Procedure

In a 40 ml scintillation vial equipped with a magnetic stir bar and fitted with a nitrogen inlet, the 5-amino-2-chloro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid 14a (107.50 mg, 0.31 mmol) was taken up in clean, dry, reagent grade dichloromethane (5.00 ml, 77.53 mmol) and the mixture was stirred until all solids were in solution. To this stirred solution was added the N,N-diisopropylethylamine (0.16 ml, 0.92 mmol) followed by the furan-2-carbonyl chloride (0.04 ml, 0.41 mmol) and the reaction was allowed to stir at room temperature overnight. The reaction was analyzed by LCMS, which showed that mixed anhydride had formed along with the desired compound. The reaction was then concentrated under reduced pressure and taken back up in methanol and the solution was then treated with saturated NaHCO3 solution and the mixture was stirred for 2 h. The mixture was then diluted with 20 ml of water and 20 ml of dichloromethane. The layers were separated and the product was extracted from the aqueous using dichloromethane (3×10 ml). The organic phases were combined, washed with brine (1×25 ml) and dried over MgSO4. The solution was filtered under vacuum and the collected solution was then concentrated under reduced pressure. The product, 2-chloro-5-[(furan-2-carbonyl)-amino]-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid 14b (135.70 mg, 0.31 mmol), was isolated as a yellowish solid and was carried on without further purification. LCMS (m/e)=439 (M+H).

Workup

  1. customIn a 40 ml scintillation vial equipped with a magnetic stir bar
  2. customfitted with a nitrogen inlet
  3. customdry

Sources & evidence

ORD record
ord-e3383a908749447b9a59d9e4f6525f16
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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