Methyl iodide → HCID 57932912、化合物

HRID 1432710ノート

反応式

HRID 1432710 の反応式
[Cl:1][C:2]1[CH:6]=[C:5]([C:7]2[N:8]([CH3:12])[N:9]=[CH:10][N:11]=2)[S:4][C:3]=1[C:13]1[N:17]2[N:18]=[C:19]([CH3:27])[CH:20]=[C:21]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:16]2=[N:15][C:14]=1[CH3:28].[CH2:29]1COCC1.[Li]C(C)(C)C.CI>CCOC(C)=O.CCCCCC>[Cl:1][C:2]1[CH:6]=[C:5]([C:7]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:29])[N:11]=2)[S:4][C:3]=1[C:13]1[N:17]2[N:18]=[C:19]([CH3:27])[CH:20]=[C:21]([CH:22]([CH2:23][CH3:24])[CH2:25][CH3:26])[C:16]2=[N:15][C:14]=1[CH3:28]

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 579330443-[3-chloro-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418306HCID 178418306、化合物

生成物 1

HCID 57932912HCID 57932912、化合物収率 42%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a −78° C. solution of 3-[3-chloro-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.30 g, 0.72 mmol) and THF (5 mL) is added 1.7 M tert-BuLi (0.47 mL, 0.80 mmol). After 15 minutes MeI (0.052 mL, 0.83 mmol) is added and the solution warmed to ambient temperature. The solution is diluted with EtOAc (40 mL), washed with brine (40 mL), dried over MgSO4, filtered and concentrated. The solution is recrystallized from acetone:hexane furnish the title compound (0.13 g, 0.30 mmol, 42%). 1H NMR (CDCl3) δ0.88 (t, J=7.5 Hz, 6H), 1.74-1.92 (m, 4H), 2.36 (s, 3H), 2.51 (s, 6H), 3.27-3.39 (m, 1H), 3.40 (s, 3H), 6.72 (s, 1H), 8.02 (s, 1H). LC/MS (m/z): calcd. for C21H25ClN6S (M+H)+: 429.2; found: 429.2.

後処理

  1. washwashed with brine (40 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe solution is recrystallized from acetone

出典と根拠

ORDレコード
ord-e56c3478e7164bd39403f1f0681c260c
出典データセット
uspto-grants-2009_11
特許番号
US07612067B2

反応ノート

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