Cyclopropanecarbonyl chloride → HCID 59618057, compound

HRID 449915Notes

Reaction equation

HRID 449915 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:19])[C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[Cl:18])[CH:5]=[CH:4][N:3]=1.[CH:20]1([C:23](Cl)=[O:24])[CH2:22][CH2:21]1>N1C=CC=CC=1>[Cl:16][C:15]1[CH:14]=[C:13]([Cl:17])[CH:12]=[C:11]([Cl:18])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:23]([CH:20]2[CH2:22][CH2:21]2)=[O:24])[CH:7]=1)=[O:19]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 67128488HCID 67128488, compound

Product 1

HCID 59618057HCID 59618057, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled (0° C.) solution of N-(2-aminopyridin-4-yl)-2,4,6-trichlorobenzamide (82 mg, 0.26 mmol) in pyridine (5 mL) under nitrogen atmosphere was added cyclopropanecarbonyl chloride (41 mg, 0.39 mmol) dropwise. The mixture was allowed to warm to room temperature, stirred overnight, and then quenched with water (15 mL). The reaction was extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with water (20 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford the desired product (10 mg, 17% yield). 1H NMR (500 MHz, CDCl3): δ 8.19 (d, J=1.5 Hz, 1H), 8.13 (d, J=6.0 Hz, 1H), 7.52 (s, 2H), 7.49-7.47 (m, 2H) 1.78 (s, 1H), 0.88-0.86 (m, 2H), 0.81-0.78 (m, J=9.5 Hz, 2H). LCMS (ESI) m/z: 367.1 [M+H+].

Workup

  1. customquenched with water (15 mL)
  2. extractionThe reaction was extracted with ethyl acetate (3×10 ml)
  3. washThe combined organic extracts were washed with water (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

Sources & evidence

ORD record
ord-42874752fe4740ecbcbe999c3bcf51fe
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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