Triethylamine → HCID 59165805, compound

HRID 2188918Notes

Reaction equation

HRID 2188918 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12](Cl)=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[Cl:15][C:16]1[N:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:17]=1[CH3:23].CCN(CC)CC>ClCCl>[Cl:15][C:16]1[N:21]=[C:20]([NH:22][C:12]([C:9]2([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:11][CH2:10]2)=[O:13])[CH:19]=[CH:18][C:17]=1[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 242737071-(4-Methoxyphenyl)cyclopropane-1-carbonyl chlorideHCID 450795946-Chloro-5-methylpyridin-2-amine

Product 1

HCID 59165805HCID 59165805, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1-(4-methoxyphenyl)cyclopropanecarbonyl chloride (21.1 mmol) in anhydrous dichloromethane (20 mL) was slowly added to a cooled solution (0° C.) of 6-chloro-5-methylpyridin-2-amine (21.2 mmol) in dichloromethane (50 mL) and Et3N (14.1 mL, 101 mmol). The reaction mixture was stirred at room temperature for 2 hours. The resulting mixture was diluted with dichloromethane and washed with water (1×30 mL), 1N NaOH (2×30 mL), 1N HCl (1×30 mL), saturated aqueous NaHCO3 (1×30 mL) and brine (1×30 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane) to yield N-(6-chloro-5-methylpyridin-2-yl)-1-(4-methoxyphenyl)cyclopropanecarboxamide (4.0 g, 63%) as a white solid. ESI-MS m/z calc. 316.1. found 317.3 (M+1)+. Retention time 1.98 minutes. 1H NMR (400 MHz, CDCl3) δ 8.08 (d, J=8.2 Hz, 1H), 7.79 (s, 1H), 7.53 (d, J=8.2 Hz, 1H), 7.39 (d, J=8.6 Hz, 2H), 6.96 (d, J=8.6 Hz, 2H), 3.88 (s, 3H), 2.31 (s, 3H), 1.72-1.69 (m, 2H), 1.19-1.16 (m, 2H).

Workup

  1. washwashed with water (1×30 mL), 1N NaOH (2×30 mL), 1N HCl (1×30 mL), saturated aqueous NaHCO3 (1×30 mL) and brine (1×30 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-28c3680afb5547359f4872b12e1e239e
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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