Triethylamine → HCID 59165805, compound

HRID 1442791Notes

Reaction equation

HRID 1442791 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 2Hours. 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-4cfd13ccc1a64b5fa3680e4ba3a52574
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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