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

Tributylphosphine → 4-(4-Chloro-2-fluorophenoxy)-7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxyquinazoline

HRID 495383
ノート
印刷プレビュー

反応式

HRID 495383 の反応式
[O:1]=[S:2]1(=[O:12])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:4][CH2:3]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[Cl:31][C:32]1[CH:51]=[CH:50][C:35]([O:36][C:37]2[C:46]3[C:41](=[CH:42][C:43](O)=[C:44]([O:47][CH3:48])[CH:45]=3)[N:40]=[CH:39][N:38]=2)=[C:34]([F:52])[CH:33]=1.C(P(CCCC)CCCC)CCC>C(OCC)C.C(Cl)Cl>[Cl:31][C:32]1[CH:51]=[CH:50][C:35]([O:36][C:37]2[C:46]3[C:41](=[CH:42][C:43]([O:11][CH2:10][CH2:9][CH2:8][N:5]4[CH2:6][CH2:7][S:2](=[O:1])(=[O:12])[CH2:3][CH2:4]4)=[C:44]([O:47][CH3:48])[CH:45]=3)[N:40]=[CH:39][N:38]=2)=[C:34]([F:52])[CH:33]=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 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 114354734-(3-Hydroxypropyl)thiomorpholine 1,1-DioxideHCID 1356162044-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline

生成物 1

HCID 219359994-(4-Chloro-2-fluorophenoxy)-7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxyquinazoline収率 69.8%

試薬・触媒・溶媒

2
HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

3-(1,1-dioxotetrahydro-4H-1,4-thiazin-4-yl)propan-1-ol (4.2 g) and 1,1′-(azodicarbonyl)dipiperidine (11.7 g) were added in turn to a mixture of 4(4-chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (5.0 g), tributylphosphine (11.1 ml) and methylene chloride (150 ml). The resultant mixture was stirred at ambient temperature overnight. The mixture was diluted with diethyl ether (300 ml) and the precipitate was removed by filtration. The filtrate was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. The material so obtained was triturated under ethyl acetate and dried to give 4-(4-chloro-2fluorophenoxy)-7-[3-(1,1-dioxotetrahydro-4H-1,4-thiazin-4-yl)propoxy]-6-methoxyquinazoline (5.4 g); NMR Spectrum: (DMSOd6) 1.86 (m, 2H), 2.65 (t, 2H), 2.92 (m, 4H), 3.08 (m, 4H), 3.97 (s, 3H), 4.26 (t, 2H), 7.4 (m, 1H), 7.42 (s, 1H), 7.56 (m, 2H), 7.68 (m, 1H), 8.54 (s, 1H).

後処理

  1. customthe precipitate was removed by filtration
  2. customThe filtrate was evaporated
  3. customthe residue was purified by column chromatography on silica using
  4. additiona 19:1 mixture of methylene chloride and methanol as eluent
  5. customThe material so obtained
  6. customwas triturated under ethyl acetate
  7. customdried

出典と根拠

ORDレコード
ord-0c875ae2e1e6419ebfc4968147179c3b
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06939866B2

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