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

Formaldehyde → 2-(4-chloro-phenyl)-6-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-6H-thieno[2,3-c]pyridin-7-one

HRID 2384917
ノート
印刷プレビュー

反応式

HRID 2384917 の反応式
F[C:2](F)(F)C(O)=O.[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:24]=[CH:23][C:22]4[CH:25]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)[S:27][C:21]=4[C:20]3=[O:35])=[CH:15][C:14]=2[O:36][CH3:37])[CH2:9]1.CO.C=O.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([C:26]2[S:27][C:21]3[C:20](=[O:35])[N:19]([C:16]4[CH:17]=[CH:18][C:13]([O:12][CH:10]5[CH2:9][N:8]([CH3:2])[CH2:11]5)=[C:14]([O:36][CH3:37])[CH:15]=4)[CH:24]=[CH:23][C:22]=3[CH:25]=2)=[CH:33][CH:32]=1
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 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 689537536-[4-(Azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one trifluoroacetate

生成物 1

HCID 248035822-(4-chloro-phenyl)-6-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-6H-thieno[2,3-c]pyridin-7-one収率 61.2%

試薬・触媒・溶媒

1
HCID 176Acetic Acid溶媒

実験手順

Mix 6-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one trifluoroacetic acid salt (210 mg, 0.48 mmol) with methanol (10 mL) and acetic acid (0.3 mL). Add a solution of formaldehyde (0.20 mL, 2.66 mmol, 37% aqueous solution) and stir the mixture for 15 min. Add sodium cyanoborohydride (110 mg, 1.75 mmol) and stir the mixture at RT overnight. Concentrate the mixture in vacuo and partition the crude material between saturated NaHCO3 (25 mL) and CH2Cl2 (25 mL). Remove the organic solution and extract the aqueous phase with additional CH2Cl2 (2×25 mL). Combine the organic solutions and concentrate in vacuo. Purify the crude material by flash chromatography, using 5% MeOH (2N NH3) in CH2Cl2 as eluent, to give 133 mg (61%) of 2-(4-chloro-phenyl)-6-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-6H-thieno[2,3-c]pyridin-7-one as a white solid.

後処理

  1. concentrationConcentrate the mixture in vacuo
  2. custompartition the crude material between saturated NaHCO3 (25 mL) and CH2Cl2 (25 mL)
  3. customRemove the organic solution
  4. extractionextract the aqueous phase with additional CH2Cl2 (2×25 mL)
  5. concentrationCombine the organic solutions and concentrate in vacuo
  6. customPurify the crude material by flash chromatography

出典と根拠

ORDレコード
ord-1c89662f58194acc80138f80fe983c9a
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263772B2

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