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Pyridine → N-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-(chloromethyl)-1,3-thiazole-4-carboxamide

HRID 1695741
ノート
印刷プレビュー

反応式

HRID 1695741 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2.N1C=CC=CC=1.[Cl:24][CH2:25][C:26]1[S:27][CH:28]=[C:29]([C:31](Cl)=[O:32])[N:30]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:17][C:31]([C:29]2[N:30]=[C:26]([CH2:25][Cl:24])[S:27][CH:28]=2)=[O:32])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 582557836-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amineHCID 597024562-(Chloromethyl)-1,3-thiazole-4-carbonyl chloride

生成物 1

HCID 58255786N-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-(chloromethyl)-1,3-thiazole-4-carboxamide収率 67.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To 6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (1.47 g) in DCM (20 ml) was added pyridine (1 ml). The reaction mixture was stirred for 5 minutes at room temperature before 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (1.21 g) in DCM (20 ml) was added dropwise over 10 minutes. The reaction mixture was stirred at room temperature for 18 hours. Saturated sodium bicarbonate solution (40 ml) was added and the reaction was stirred vigorously before the organic layer was separated using a hydrophobic frit. The aqueous layer was extracted with further DCM and the combined organic layers were evaporated to dryness. The residual solid was dried on a high vacuum line before triturating with cyclohexane to give the title compound (1.52 g).

後処理

  1. additionwas added dropwise over 10 minutes
  2. stirringthe reaction was stirred vigorously before the organic layer
  3. customwas separated
  4. extractionThe aqueous layer was extracted with further DCM
  5. customthe combined organic layers were evaporated to dryness
  6. customThe residual solid was dried on a high vacuum line
  7. custombefore triturating with cyclohexane

出典と根拠

ORDレコード
ord-da4ba152ae204accaca5ff5c985e463e
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

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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