Anisole → 5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol

HRID 911058노트

반응식

HRID 911058 반응식
COC1C=CC(C[S:8][C:9]2[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH:16][C:17]3[S:18][CH:19]=[C:20]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:21]=3)[CH:10]=2)=CC=1.C1(OC)C=CC=CC=1.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[Br:15][C:14]1[C:9]([SH:8])=[CH:10][C:11]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:21]=2)=[N:12][CH:13]=1

참가 물질

5

반응물 3

HCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 866347724-(4-methoxybenzylthio)-5-bromo-N-(4-phenethylthiazol-2-yl)pyridine-2-amine

생성물 1

HCID 1785277275-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol수율 72.2%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

반응 조건

온도
75 °C

실험 절차

4-(4-methoxybenzylthio)-5-bromo-N-(4-phenethylthiazol-2-yl)pyridine-2-amine (1.23 g, 2.4 mmol) was dissolved in TFA (10 mL):anisole (2 mL) (5:1). The reaction mixture was stirred at 75° C. overnight, then neutralized with solid NaHCO3, extracted with EtOAc, dried, and concentrated. The crude material was triturated in MeOH and filtered. The filtrate was further concentrated and triturated again with MeOH. The solids were combined and dried to give the desired product (0.68 g, 72% yield).

후처리

  1. extractionextracted with EtOAc
  2. customdried
  3. concentrationconcentrated
  4. customThe crude material was triturated in MeOH
  5. filtrationfiltered
  6. concentrationThe filtrate was further concentrated
  7. customtriturated again with MeOH
  8. customdried

출처 및 근거

ORD 기록
ord-a0b7f573027c4478b41296cc46429dfd
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022222B2

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