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

Cesium carbonate → 2-(2-Chloro-6-fluorophenyl)-N-(2-methyl-6-morpholinopyrimidin-4-yl)thiazolo[5,4-c]pyridin-4-amine

HRID 2366199
ノート
印刷プレビュー

反応式

HRID 2366199 の反応式
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH3:19][C:20]1[N:25]=[C:24]([NH2:26])[CH:23]=[C:22]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:11]=1[C:9]1[S:8][C:7]2[C:2]([NH:26][C:24]3[CH:23]=[C:22]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[N:21]=[C:20]([CH3:19])[N:25]=3)=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 328000292-Methyl-6-morpholinopyrimidin-4-amineHCID 866689904-Bromo-2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridine

生成物 1

HCID 569532982-(2-Chloro-6-fluorophenyl)-N-(2-methyl-6-morpholinopyrimidin-4-yl)thiazolo[5,4-c]pyridin-4-amine
収率 24%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

To a microwave tube was added 4-bromo-2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridine (0.050 g, 1.5 mmol), 2-methyl-6-morpholinopyrimidin-4-amine (0.043 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos (0.017 g, 0.034 mmol) and Cs2CO3 (0.11 g, 0.34 mmol) in dioxane (2.0 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160° C. for 2 hours. After cooling to room temperature, the solid was removed via filtration and the filtrate was concentrated under reduced pressure. The residue was purified with reverse phase column chromatography, eluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3 to give the desired product as a yellow solid (0.016 g, 24% yield). 1H NMR (500 MHz, DMSO-d6): δ 10.22 (s, 1H), 8.38 (d, J=5.5 Hz, 1H), 7.75 (d, J=5.5 Hz, 1H), 7.73-7.68 (m, 1H), 7.62-7.60 (m, 1H), 7.54-7.50 (m, 1H), 6.75 (s, 1H), 3.69-3.67 (m, 4H), 3.52-3.50 (m, 4H), 2.33 (s, 3H). LCMS (Method A): RT=6.16 min, m/z: 457.1 [M+H+].

後処理

  1. customThe mixture was degassed with N2 for 10 minutes
  2. customirradiated in a microwave reactor at 160° C. for 2 hours
  3. customthe solid was removed via filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified with reverse phase column chromatography
  6. washeluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3

出典と根拠

ORDレコード
ord-217b0ddde4234a638d737bd29ac6238c
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08697708B2

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