Acetic Acid → 3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]-2-(methyloxy)aniline

HRID 590121노트

반응식

HRID 590121 반응식
C(OC(=O)[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[N:14]=[C:15]([CH:25]([CH3:27])[CH3:26])[S:16][C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[N:19]=2)[C:8]=1[O:28][CH3:29])C=C.C(O)(=O)C.C([SnH](CCCC)CCCC)CCC>C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:24][C:20]1[N:19]=[C:18]([C:17]2[S:16][C:15]([CH:25]([CH3:27])[CH3:26])=[N:14][C:13]=2[C:9]2[C:8]([O:28][CH3:29])=[C:7]([CH:12]=[CH:11][CH:10]=2)[NH2:6])[CH:23]=[CH:22][N:21]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 5948TributylstannaneHCID 579896912-Propen-1-yl[3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]-2-(methyloxy)phenyl]carbamate

생성물 1

HCID 579898673-[5-(2-Chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]-2-(methyloxy)aniline수율 123.2%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

To the solution of 2-propen-1-yl[3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]-2-(methyloxy)phenyl]carbamate (12.1 g, 22.5 mmol) in DCM (200 mL), acetic acid (3.8 mL, 66.6 mmol), Pd(PPh3)2Cl2 (0.45 g, 0.56 mmol) were added. Then tri-n-butyl tin hydride (8.5 mL, 33 mmol) was added dropwise to the mixture at 0° C. The mixture was stirred at rt for 30 min. The reaction was quenched by added the saturated NaHCO3 (200 mL) slowly. The two layers were separated. The aqueous layer was extracted with DCM (200 mL×2). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was washed with petroleum ether (500 mL) to afford the title compound of Step G (10 g, 60.8% yield), which was used directly in the next step.

후처리

  1. customThe reaction was quenched
  2. additionby added the saturated NaHCO3 (200 mL) slowly
  3. customThe two layers were separated
  4. extractionThe aqueous layer was extracted with DCM (200 mL×2)
  5. washThe combined organic layers were washed with water and brine successively
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give the crude product, which
  10. washwas washed with petroleum ether (500 mL)

출처 및 근거

ORD 기록
ord-ac60338ade0d491888d745283742737b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233956B2

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