Tetrahydrofuran → HCID 69308215、化合物

HRID 860453ノート

反応式

HRID 860453 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=3)[N:12]=[C:13]([CH3:24])[C:14]=2[CH2:15][CH2:16][CH2:17][CH2:18]C(OCC)=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[BH4-].[Li+].[O:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH2:28]([C:25]1[N:11]2[N:12]=[C:13]([CH3:24])[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:34][CH2:33][OH:32])=[C:9]([C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=3)[C:1]#[N:2])[C:10]2=[CH:27][CH:26]=1)[CH3:29].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=3)[N:12]=[C:13]([CH3:24])[C:14]=2[CH2:15][CH2:16][CH2:36][CH2:35][CH2:34][CH2:33][OH:32])[CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydride2 回HCID 9977651Ethyl 5-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate

生成物 2

HCID 69307009HCID 69307009、化合物収率 31.9%HCID 69308215HCID 69308215、化合物収率 64.5%

実験手順

To a solution of ethyl 5-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate (45 mg) in tetrahydrofuran (1 mL) was added lithium borohydride (5 mg) in an ice-water bath. Then the reaction mixture was stirred at ambient temperature. After 2 hours, another lithium borohydride (5 mg) was added therein and was stirred overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and was evaporated in vacuo. The residue was purified by p-TLC (hexane-ethyl acetate=1-1) to give 3-[7-ethyl-3-(6-hydroxyhexyl)-2-methylpyrrolo[1,2-b]pyridazin-4-yl]benzonitrile (26 mg, 64.5%) as an yellow oil and 6-{4-[3-(aminomethyl)phenyl]-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl}-1-hexanol (13 mg, 31.9%) as a yello solid.

後処理

  1. stirringwas stirred overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customwas evaporated in vacuo
  6. customThe residue was purified by p-TLC (hexane-ethyl acetate=1-1)

出典と根拠

ORDレコード
ord-1d9995f062f74472a900bd8ed8ed118a
出典データセット
uspto-grants-2006_12
特許番号
US07153854B2

反応ノート

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