Dichloromethane → Imidazo[2,1-b]thiazole,5-ethyl-6-[[2-(6-fluoro-2-pyridinyl)-1h-imidazol-1-yl]methyl]-

HRID 586379노트

반응식

HRID 586379 반응식
Cl[CH2:2][C:3]1[N:4]=[C:5]2[N:9]([C:10]=1[CH2:11][CH3:12])[CH:8]=[CH:7][S:6]2.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)[N:15]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CN(C=O)C.[Cl-].[Na+].O>[CH2:11]([C:10]1[N:9]2[C:5]([S:6][CH:7]=[CH:8]2)=[N:4][C:3]=1[CH2:2][N:24]1[CH:23]=[CH:22][N:21]=[C:20]1[C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([F:13])[N:15]=1)[CH3:12]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 223351136-Chloromethyl-5-ethyl-imidazo[2,1-b]thiazole

생성물 1

HCID 22335063Imidazo[2,1-b]thiazole,5-ethyl-6-[[2-(6-fluoro-2-pyridinyl)-1h-imidazol-1-yl]methyl]-수율 16.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of 6-chloromethyl-5-ethyl-imidazo[2,1-b]thiazole (120 mg, 0.6 mmol), 2-fluoro-6-(1H-imidazol-2-yl)pyridine (82 mg, 0.6 mmol) and potassium carbonate (278 mg, 2.4 mmol) in DMF (6 mL) is stirred at room temperature for 48 h. Brine (15 mL) and methylene chloride (20 mL) are added. The organic layer is separated and the aqueous layer is extracted with methylene chloride (2×20 mL). The combined organic layers are washed with brine (3×15 mL) and dried. The solvent is removed in vacuo. The residue is purified by preparative TLC to give 32 mg of 5-ethyl-6-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-imidazo[2,1-b]thiazole as an oil. 1H NMR (CDCl3): 8.10, dd (1H); 7.82, dd (1H); 7.35, d (1H); 7.26, d (1H); 7.12, d (1H); 6.83, dd (1H); 6.80, d (1H); 5.92, s (2H); 2.90, q (2H); 1.07, t (3H).

후처리

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with methylene chloride (2×20 mL)
  3. washThe combined organic layers are washed with brine (3×15 mL)
  4. customdried
  5. customThe solvent is removed in vacuo
  6. customThe residue is purified by preparative TLC

출처 및 근거

ORD 기록
ord-c6adbdbc22724a6c988dd54e663d2beb
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936617B2

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