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

HRID 911058ノート

反応式

HRID 911058 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a0b7f573027c4478b41296cc46429dfd
出典データセット
uspto-grants-2011_09
特許番号
US08022222B2

反応ノート

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