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

Triethylamine → (E)-3-((7-chloro-3-(3-morpholino-3-oxoprop-1-enyl)imidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one

HRID 80634
ノート
印刷プレビュー

反応式

HRID 80634 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](I)=[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:15]=4[N:14]([CH:21]4[CH2:23][CH2:22]4)[C:13]3=[O:24])[N:10]=[C:4]2[CH:3]=1.ClC1C=CN=C(N)C=1.CCN(CC)CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:60]1[CH2:65][CH2:64][N:63]([C:66](=[O:69])[CH:67]=[CH2:68])[CH2:62][CH2:61]1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](/[CH:68]=[CH:67]/[C:66]([N:63]3[CH2:64][CH2:65][O:60][CH2:61][CH2:62]3)=[O:69])=[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:15]=4[N:14]([CH:21]4[CH2:23][CH2:22]4)[C:13]3=[O:24])[N:10]=[C:4]2[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 98723AcryloylmorpholineHCID 5818662-Amino-4-chloropyridineHCID 679876583-((7-chloro-3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one

生成物 1

HCID 57410366
(E)-3-((7-chloro-3-(3-morpholino-3-oxoprop-1-enyl)imidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one
収率 92%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-((7-chloro-3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one 12-a (prepared following the 3-step synthesis used for 7-b, using 4-chloro-2-aminopyridine instead of 2-aminopyridine in step 1) and Et3N (2.218 mL, 8 eq) in DMF (30 mL) was degassed with nitrogen for fifteen minutes. Then palladium acetate (45 mg, 0.1 eq), triphenylphosphine (173 mg, 0.33 eq) and 1-morpholinoprop-2-en-1-one (2.516 mL, 10 eq) were added and stirring in a closed vessel was allowed at 80° C. during two hours. After cooling the mixture was quenched with ice water. After one hour stirring the precipitate was filtered off and dried in vacuo. The solid was purified over silica with dichloromethane/methanol-NH3 98/2 as eluent to provide the target compound P24 in 92% yield (884 mg). m/z=479 (M+H)+;

後処理

  1. customthe 3-step synthesis
  2. customwas degassed with nitrogen for fifteen minutes
  3. temperatureAfter cooling the mixture
  4. customwas quenched with ice water
  5. stirringAfter one hour stirring the precipitate
  6. filtrationwas filtered off
  7. customdried in vacuo
  8. customThe solid was purified over silica with dichloromethane/methanol-NH3 98/2 as eluent
  9. customto provide the target compound P24 in 92% yield (884 mg)

出典と根拠

ORDレコード
ord-0819504441b64db8a15f38ec8030cda9
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846672B2

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