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

Sodium Carbonate → N-{6-[5-Amino-6-(methyloxy)-3-pyridinyl]-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide

HRID 1695742
ノート
印刷プレビュー

反応式

HRID 1695742 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([NH:21][C:22]([C:24]2[N:25]=[C:26]([CH2:29][N:30]3[CH2:35][C@H:34]([CH3:36])[O:33][C@H:32]([CH3:37])[CH2:31]3)[S:27][CH:28]=2)=[O:23])[CH:3]=1.[CH3:38][O:39][C:40]1[C:45]([NH2:46])=[CH:44][C:43](B2OC(C)(C)C(C)(C)O2)=[CH:42][N:41]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O>[NH2:46][C:45]1[CH:44]=[C:43]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][N:8]3[S:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)(=[O:12])=[O:13])=[C:4]([NH:21][C:22]([C:24]3[N:25]=[C:26]([CH2:29][N:30]4[CH2:35][C@H:34]([CH3:36])[O:33][C@H:32]([CH3:37])[CH2:31]4)[S:27][CH:28]=3)=[O:23])[CH:3]=2)[CH:42]=[N:41][C:40]=1[O:39][CH3:38]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 58255797N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamideHCID 595579202-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine

生成物 1

HCID 58255776
N-{6-[5-Amino-6-(methyloxy)-3-pyridinyl]-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide
収率 44.3%

試薬・触媒・溶媒 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide (4 g), 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (1.8 g), sodium carbonate (2.8 g) and Pd(dppf)Cl2 (0.48 g) were weighed to a 500 ml round-bottomed flask and 1,4-dioxane (150 ml) and water (150 ml) were added. The reaction was heated to 80° C. for 2 hours. The reaction was cooled then passed through a 10 g silica cartridge, washing with DCM:methanol. The reaction was concentrated to leave only the aqueous phase. DCM was added and the product extracted. The DCM was passed through a hydrophobic frit, then evaporated to dryness. The residue was purified on silica chromatography eluting with 0-6% methanol in DCM over 30 mins. Product containing fractions were combined and evaporated to dryness. The residue was repurified by silica chromatography using a gradient of 1.5-5% methanol in DCM over 30 mins. Product containing fractions were combined and evaporated to dryness to give title compound (1.9 g).

後処理

  1. temperatureThe reaction was cooled
  2. washwashing with DCM
  3. concentrationThe reaction was concentrated
  4. customto leave only the aqueous phase
  5. extractionthe product extracted
  6. customevaporated to dryness
  7. customThe residue was purified on silica chromatography
  8. washeluting with 0-6% methanol in DCM over 30 mins
  9. additionProduct containing fractions
  10. customevaporated to dryness
  11. customThe residue was repurified by silica chromatography
  12. customover 30 mins
  13. additionProduct containing fractions
  14. customevaporated to dryness

出典と根拠

ORDレコード
ord-c89d528c19224cc3993427c40993eb86
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163743B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート