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

1,8-Diazabicyclo(5.4.0)undec-7-ene → (4-Chloro-phenyl)-{4-[(3S,4S)-4-hydroxy-1-(6-methoxy-quinazolin-4-yl)-pyrrolidin-3-yl]-piperazin-1-yl}-methanone

HRID 1361501
ノート
印刷プレビュー

反応式

HRID 1361501 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH:20]([OH:21])[CH2:19][NH:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.Cl[C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[C:41]([O:44][CH3:45])[CH:42]=2)[N:37]=[CH:36][N:35]=1.ClC1C2C(=CC=C(OC)C=2)N=C(C)N=1>CO.CCOC(C)=O.CCOCC.C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C@@H:16]3[C@@H:20]([OH:21])[CH2:19][N:18]([C:34]4[C:43]5[C:38](=[CH:39][CH:40]=[C:41]([O:44][CH3:45])[CH:42]=5)[N:37]=[CH:36][N:35]=4)[CH2:17]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][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

9

反応物 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2 回HCID 111831744-Chloro-6-methoxyquinazolineHCID 122776024-Chloro-6-methoxy-2-methylquinazolineHCID 66968375(4-Chloro-phenyl)-[4-(4-hydroxy-pyrrolidin-3-yl)-piperazin-1-yl]-methanone2 回

生成物 1

HCID 58451141(4-Chloro-phenyl)-{4-[(3S,4S)-4-hydroxy-1-(6-methoxy-quinazolin-4-yl)-pyrrolidin-3-yl]-piperazin-1-yl}-methanone
収率 50%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To 0.326 mmoles of (4-Chloro-phenyl)-[4-(4-hydroxy-pyrrolidin-3-yl)-piperazin-1-yl]-methanone (synthesis described above in Example 5), add 1.6 mL acetonitrile and 1.6 mmoles of DBU. The stirred solution was cooled in ice and then 0.358 mmoles of 4-chloro-6-methoxy-quinazoline was added and the reaction mixture was allowed to stir for a period of 2.5 hours. To 0.326 mmoles of (4-Chloro-phenyl)-[4-(4-hydroxy-pyrrolidin-3-yl)-piperazin-1-yl]-methanone, add 1.6 mL acetonitrile and 1.63 mmoles of DBU. The stirred solution was cooled in ice and then 0.358 mmoles of 4-chloro-6-methoxy-2-methyl-quinazoline (from Step 2 above) was added and the reaction mixture was allowed to stir for a period of 2.5 hours. For the reaction workup, the reaction mixture was diluted with methanol and concentrated on the rotavap. To the concentrate about 30 mL of water was added and was extracted with 40 mL EtOAc. The organic layer was separated and washed with 30 mL of 1M aq K2CO3 solution, and brine, dried over MgSO4 and excess solvent was removed on rotavap to yield a crude oil. This was diluted with about 2 mL EtOAc and about 8 mL ether was added and the white solid obtained was filtered off and vaccum dried to give the title compound in 50% yield. LC-MS: m/z=468 (M++1).

後処理

  1. temperatureThe stirred solution was cooled in ice
  2. temperatureThe stirred solution was cooled in ice
  3. stirringto stir for a period of 2.5 hours
  4. concentrationconcentrated on the rotavap
  5. additionTo the concentrate about 30 mL of water was added
  6. extractionwas extracted with 40 mL EtOAc
  7. customThe organic layer was separated
  8. washwashed with 30 mL of 1M aq K2CO3 solution, and brine
  9. dry with materialdried over MgSO4 and excess solvent
  10. customwas removed on rotavap
  11. customto yield a crude oil
  12. additionwas added
  13. customthe white solid obtained
  14. filtrationwas filtered off
  15. customvaccum dried

出典と根拠

ORDレコード
ord-223140f6d18e4ff0a0dbc8a8ac6d7089
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07880002B2

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