ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Water → 6,6-Dimethyl-2-(6-{1-[2-(morpholin-4-yl)ethyl]-1h-pyrazol-4-yl}-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885959
ノート
印刷プレビュー

反応式

HRID 885959 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[CH2:14]C(C)(C)N[C:17](=O)[C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[N:34][N:35]([CH2:37][CH2:38][N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[CH:36]=2)O1.C([O-])([O-])=O.[K+].[K+].[OH2:52]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:5][C:6]1([CH3:23])[NH:7][C:14](=[O:52])[C:13]2[S:12][C:11]([N:7]3[C:6]4[CH:23]=[C:2]([C:32]5[CH:33]=[N:34][N:35]([CH2:37][CH2:38][N:39]6[CH2:40][CH2:41][O:42][CH2:43][CH2:44]6)[CH:36]=5)[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)=[N:19][C:18]=2[CH2:17]1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 177499241-(2-Morpholinoethyl)-1H-pyrazole-4-boronic acid pinacol esterHCID 685972362-(6-Bromo-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydro-[1,3]thiazolo[5,4-d]pyridin-4(5h)-one

生成物 1

HCID 671876196,6-Dimethyl-2-(6-{1-[2-(morpholin-4-yl)ethyl]-1h-pyrazol-4-yl}-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one
収率 41%

試薬・触媒・溶媒 4

HCID 74236Tetrabutylammonium Bromide触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A stirred solution of Example 39 (0.1 g, 0.326 mmol), 4-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethyl}morpholine (0.051 g, 0.165 mmol), K2CO3 (0.054 g, 0.395 mmol), tetra-n-butylammonium bromide (0.122 g, 0.377 mmol), tetrakis(triphenylphosphine)palladium(0) (0.007 g, 0.006 mmol) and H2O (0.5 mL) in THF (1 mL) was heated at 125° C. in a sealed vessel for 2.5 days. After cooling to r.t. the reaction mixture was diluted with EtOAc and washed with water and brine. The organic fraction was dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 0-100% [9:1 EtOAc/MeOH]/heptane) followed by trituration with Et2O gave the title compound (0.026 g, 41%) as a white solid. δH (CDCl3) 8.00 (1H, d, J 2.1 Hz), 7.72 (1H, s), 7.68 (1H, s), 7.20 (1H, dd, J 8.5 and J 2.1 Hz), 6.97 (1H, d, J 8.5 Hz), 5.27 (1H, br. s), 4.39-4.26 (4H, m), 4.25-4.19 (2H, m), 3.78-3.69 (4H, m), 2.95-2.83 (4H, m), 2.61-2.49 (4H, m), 1.42 (6H, s). LCMS (ES+) 495.5 (M+H)+, RT 2.04 minutes (Method 1).

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic fraction was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 0-100% [9:1 EtOAc/MeOH]/heptane)

出典と根拠

ORDレコード
ord-f48a7cfd31564d4bb715fd711177075c
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08242116B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート