Diethyl Ether → 1-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol

HRID 1675053ノート

反応式

HRID 1675053 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([F:21])([F:20])[F:19])=[N:16][N:17]=2)[N:14]=1.CCN(C(C)C)C(C)C.CCOCC>CN(C=O)C>[F:20][C:18]([F:19])([F:21])[C:15]1[N:13]2[N:14]=[C:9]([N:5]3[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]3)[CH:10]=[CH:11][C:12]2=[N:17][N:16]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazine

生成物 1

HCID 245876321-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
125 °C

実験手順

4-Hydroxypiperidine (10.91 g, 107.84 mmol) was added to 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (20 g, 89.87 mmol) and DIPEA (23.48 mL, 134.80 mmol) in DMF (200 mL). The resulting solution was stirred at 125° C. for 2 hours. The reaction mixture was evaporated to dryness, redissolved in DCM and purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to give a beige solid which was stirred with ether then filtered to afford 1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol (22.64 g, 88%) as a solid.

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in DCM
  3. custompurified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM
  4. customPure fractions were evaporated to dryness
  5. customto give a beige solid which
  6. filtrationthen filtered

出典と根拠

ORDレコード
ord-4b591daf562743a292a7466cc35dea90
出典データセット
uspto-grants-2011_08
特許番号
US08003649B2

反応ノート

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