Triethylamine → 1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-ol

HRID 16007

反応式

HRID 16007 の反応式
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.[NH:22]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]1.C(N(CC)CC)C>CC(O)C>[N:18]1[C:19]2[C:14](=[CH:13][C:12]([CH2:11][N:8]3[C:6]4=[N:7][C:2]([N:22]5[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]5)=[CH:3][N:4]=[C:5]4[N:10]=[N:9]3)=[CH:21][CH:20]=2)[CH:15]=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 982104-HydroxypyrrolidineHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

生成物 1

HCID 593418001-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-ol収率 99.5%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
70 °C

実験手順

A mixture of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (5.00 g, 14.7 mmol), pyrrolidin-3-ol (2.55 g, 29.3 mmol), and triethylamine (4.09 mL, 29.3 mmol) in 2-propanol (32 mL) was heated in the microwave for 30 minutes at 70° C. in two vials. The reaction mixtures were combined and concentrated. The crude product was purified by flash chromatography using a Horizon purification system in three batches (2×40M and 1×40S columns) eluting with chloroform/methanol (0.1-8%). The resulting solid was dissolved in chloroform containing 0.1% methanol (810 mL) and washed with water and 1:1 water:brine, dried (MgSO4), filtered and concentrated to afford 1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-ol (5.08 g, 99%).

後処理

  1. customThe reaction mixtures
  2. concentrationconcentrated
  3. customThe crude product was purified by flash chromatography
  4. customa Horizon purification system in three batches (2×40M and 1×40S columns)
  5. washeluting with chloroform/methanol (0.1-8%)
  6. dissolutionThe resulting solid was dissolved in chloroform containing 0.1% methanol (810 mL)
  7. washwashed with water and 1:1 water
  8. dry with materialbrine, dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-f089dea19870496996dd805e2acbbcdb
出典データセット
uspto-grants-2010_06
特許番号
US07732604B2

関連ノート

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