1,1'-Carbonyldiimidazole → N-(6-(2-(3-fluorophenyl)piperidin-1-yl)imidazo[1,2-b]pyridazin-3-yl)-3-hydroxyazetidine-1-carboxamide

HRID 588541ノート

反応式

HRID 588541 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([NH2:23])=[CH:21][N:22]=3)[N:19]=2)[CH:5]=[CH:6][CH:7]=1.C1N=CN([C:29]([N:31]2[CH:35]=N[CH:33]=[CH:32]2)=[O:30])C=1.Cl.N1CC([OH:41])C1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([NH:23][C:29]([N:31]4[CH2:32][CH:33]([OH:41])[CH2:35]4)=[O:30])=[CH:21][N:22]=3)[N:19]=2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 673077316-(2-(3-Fluorophenyl)piperidin-1-yl)imidazo[1,2-b]pyridazin-3-amine

生成物 1

HCID 58334484N-(6-(2-(3-fluorophenyl)piperidin-1-yl)imidazo[1,2-b]pyridazin-3-yl)-3-hydroxyazetidine-1-carboxamide収率 52.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a DCM (2 mL) solution of 6-(2-(3-fluorophenyl)piperidin-1-yl)imidazo[1,2-b]pyridazin-3-amine (45 mg, 0.14 mmol) was added CDI (35 mg, 0.22 mmol) at ambient temperature in one portion. After stirring for five hours, azetidin-3-ol hydrochloride (54 mg, 0.33 mmol) was added in one portion, followed by DIEA (0.05 mL, 0.29 mmol), and the reaction was stirred at ambient temperature overnight. The reaction was diluted with DCM, washed with water, dried over Na2SO4 and concentrated. The crude product was purified by reversed phase column, eluting with 0 to 55% CH3CN/water to obtain the desired product as a solid (30 mg, 51% yield). MS (apci) m/z=411.2 (M+H).

後処理

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by reversed phase column
  6. washeluting with 0 to 55% CH3CN/water

出典と根拠

ORDレコード
ord-f5b62cc92c2449678dfbb60e33225dab
出典データセット
uspto-grants-2016_01
特許番号
US09227975B2

反応ノート

読み込み中…