Trimethylsilyldiazomethane → 5-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester

HRID 1500701노트

반응식

HRID 1500701 반응식
[Cl:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:13]=2[F:22])[C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH3:23][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:23][O:9][C:8]([C:5]1[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:19])([CH3:21])[CH3:20])=[CH:14][C:13]=2[F:22])=[N:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:10]

참가 물질

6

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 591401225-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid

생성물 1

HCID 591401805-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester수율 71.1%

시약·촉매·용매 3

HCID 887Methanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid (2.95 g, 8.68 mmol) in methanol (50 mL) and toluene (100 mL) at 0° C. under N2 was added a solution of 2M trimethylsilyldiazomethane in hexanes (9.55 mL, 19.0 mmol, 2.2 eq.), and the reaction mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine, then dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 50% ethyl acetate in hexane) to give the desired compound as a yellow solid (2.18 g, 71.1%). 1H NMR (CDCl3, 400 MHz) δ ppm 10.54 (s, 1H), 8.36 (t, J=7.86 Hz, 1H), 8.06 (s, 1H), 7.34-7.26 (m, 2H), 4.05 (s, 3H), 0.28 (s, 9H); LCMS (method D1) RT=1.38 min, [M+H]+=354.

후처리

  1. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-fe4c3d728ea445708710d16a16f1c223
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206174B2

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